84371-57-3

Basic information

• Product Name: (5α,10α,17β)-5,10-Epoxy-17-hydroxy-17-(1-propyn-1-yl)-estr-9(11)-en-3-one Cyclic 1,2-Ethanediyl Acetal
• Synonyms: (5α,10α,17β)-5,10-Epoxy-17-hydroxy-17-(1-propyn-1-yl)-estr-9(11)-en-3-one Cyclic 1,2-Ethanediyl Acetal;5α,10α-Epoxy-17β-hydroxy-17-(1-propynyl)estr-9(11)-en-3-one Cyclic Ethylene Acetal;5α,10α-Epoxy-3,3-(ethylenedioxy)-17β-hydroxy-17α-(1-propynyl)-9(11)-estrene;NRUIWWWJNIPUBD-XZJZWBLTSA-N
• CAS NO: 84371-57-3
• Molecular Formula: C23H30O4
• Molecular Weight: 370.4819
• Product Categories: Intermediates;Steroids
• Mol File: 84371-57-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 122-125°C
• Appearance: /
• Storage Temp.: Refrigerator
• CAS DataBase Reference: (5α,10α,17β)-5,10-Epoxy-17-hydroxy-17-(1-propyn-1-yl)-estr-9(11)-en-3-one Cyclic 1,2-Ethanediyl Acetal(CAS DataBase Reference)
• NIST Chemistry Reference: (5α,10α,17β)-5,10-Epoxy-17-hydroxy-17-(1-propyn-1-yl)-estr-9(11)-en-3-one Cyclic 1,2-Ethanediyl Acetal(84371-57-3)
• EPA Substance Registry System: (5α,10α,17β)-5,10-Epoxy-17-hydroxy-17-(1-propyn-1-yl)-estr-9(11)-en-3-one Cyclic 1,2-Ethanediyl Acetal(84371-57-3)

Safety Data

• Hazardous Substances Data: 84371-57-3(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Uses

Intermediate in the preparation of Mifepristone derivatives.

Synthetic route

1-propynylmagnesium bromide (16466-97-0, 13254-27-8) + (5'R,10'R,13'S)-13'-methyl-1',2',6',7',8',12',13',14',15',16'-decahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one (39931-88-9, 116003-08-8, 39931-87-8) → (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3)

Conditions	Yield
Stage #1: 1-propynylmagnesium bromide; (5'R,10'R,13'S)-13'-methyl-1',2',6',7',8',12',13',14',15',16'-decahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one In tetrahydrofuran at 0℃; for 2h; Stage #2: With ammonium chloride In water	100%

(8S,13S,14S,17S)-13-methyl-17-(prop-1-yn-1-yl)-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol (84371-69-7) → (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane	35%
With disodium hydrogenphosphate; dihydrogen peroxide; Hexafluoroacetone In dichloromethane; water at 0 - 20℃; for 2.16667h;	1.8 g

(5'R,10'R,13'S,16'R)-13',16'-dimethyl-1',2',6',7',8',12',13',14',15'-nonahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one (639520-94-8) + 1-propynylmagnesium bromide (16466-97-0, 13254-27-8) → (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3)

Conditions	Yield
Stage #1: (5'R,10'R,13'S,16'R)-13',16'-dimethyl-1',2',6',7',8',12',13',14',15'-nonahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one; 1-propynylmagnesium bromide In tetrahydrofuran at 0℃; for 2.5h; Stage #2: With ammonium chloride In tetrahydrofuran; water	29%

1-propynyl lithium (4529-04-8) + (5'R,10'R,13'S)-13'-methyl-1',2',6',7',8',12',13',14',15',16'-decahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one (39931-88-9, 116003-08-8, 39931-87-8) → (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3)

Conditions	Yield
In tetrahydrofuran; hexane for 1h; Yield given;

ethylene deltenone (5571-36-8) → (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / tetrahydrofuran 2: 35 percent / m-CPBA / CH2Cl2 View Scheme
Multi-step reaction with 2 steps 1: 76.1 percent / 30percent H2O2, hexachloroacetone / CH2Cl2 / 72 h 2: tetrahydrofuran; hexane / 1 h View Scheme
Multi-step reaction with 2 steps 1: tetrahydrofuran / 0 - 20 °C 2: Hexafluoroacetone; disodium hydrogenphosphate; dihydrogen peroxide / dichloromethane; water / 2.17 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: tetrahydrofuran / 0 - 25 °C / Inert atmosphere 2: Hexafluoroacetone; dihydrogen peroxide / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; aq. phosphate buffer / 2.17 h / 0 - 20 °C / Inert atmosphere View Scheme

(8S,13S,14S,17S)-13-methyl-17-(prop-1-yn-1-yl)-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol (84371-69-7) → 5β,10β-epoxy-3,3-ethylenedioxy-17β-hydroxy-17α-(1-propynyl)estra-9(11)-ene + (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3)

Conditions	Yield
With pyridine; 1,1,1,3,3,3-hexachloro-propan-2-one; Br(1-)*C26H29N2O(1+); dihydrogen peroxide In dichloromethane; water at 20℃; for 48h; optical yield given as %de; diastereoselective reaction;
With dihydrogen peroxide; Hexafluoroacetone In aq. phosphate buffer; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 0 - 20℃; for 2.16667h; Inert atmosphere;	A n/a B n/a

4-(N-isopropyl-N-methylamino)phenyl bromide (61684-98-8) + (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → 5α-17β-dihydroxy-11β-[4-(N-isopropyl-N-methylamino)phenyl]-17α-ethynyl-3,3-(ethane-1,2-diyldioxy)-estra-9-ene (883565-88-6)

Conditions	Yield
Stage #1: 4-(N-isopropyl-N-methylamino)phenyl bromide With magnesium In tetrahydrofuran for 0.416667h; Heating; Stage #2: (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol With copper(l) chloride In tetrahydrofuran at 6 - 7℃; for 0.5h;	100%

(5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) + 4-(N-tert-butyloxycarbonyl-N-methylamino)phenyl bromide (639520-70-0) → tert-butyl 4-((5R,11R,13S,17S)-5,17-dihydroxy-13-methyl-17-prop-1-ynyl-1,2,4,5,6,7,8,11,12,13,14,15,16,17-tetradecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-11-yl)phenyl(methyl)carbamate (639520-75-5)

Conditions

Yield

Stage #1: 4-(N-tert-butyloxycarbonyl-N-methylamino)phenyl bromide With iodine; magnesium In tetrahydrofuran at 20℃; for 0.416667h; Heating / reflux; Stage #2: With copper(l) iodide In tetrahydrofuran at 0℃; for 0.0333333h; Stage #3: (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol With ammonium chloride more than 3 stages;

90%

4-(N-isopropyl-N-trimethylsilylamino)phenyl bromide (883565-85-3) + (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → 5α-17β-dihydroxy-11β-[4-(N-isopropyl-N-trimethylsilylamino)phenyl]-17α-ethynyl-3,3-(ethane-1,2-diyldioxy)-estra-9-ene (883565-86-4)

Conditions	Yield
Stage #1: 4-(N-isopropyl-N-trimethylsilylamino)phenyl bromide With magnesium In tetrahydrofuran for 0.416667h; Heating; Stage #2: (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol With copper(l) chloride In tetrahydrofuran at 6 - 7℃; for 0.5h;	75%

(4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)magnesium bromide (36637-44-2) + (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → C34H44O6 (934415-53-9)

Conditions	Yield
With copper(l) chloride In tetrahydrofuran	53%

(5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) + p-N-trimethylsilyl-N-methylaminophenylmagnesium bromide → 11β-(4-methylaminophenyl)-<3,3-(1,2-ethylenedioxybisoxy)>-17α-(1-propynyl)-estra-9-en-5α,7β-diol (104004-98-0)

Conditions	Yield
With ammonium chloride; copper(l) chloride 1.) THF, 6 h, 2.) THF; Yield given. Multistep reaction;

4-(N-methyl-N-cyclohexylamino)phenyl magnesium bromide (329971-57-5) + (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N-methyl-N-cyclohexylamino)phenyl]-17α-(1-propynyl)-9(10)-estrene (329971-39-3)

Conditions	Yield
With copper dichloride In tetrahydrofuran at 5℃; for 5h;

(5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → 17β-hydroxy-11β-[4-hydroxyphenyl]-17α-(1-propinyl)-estra-4,9-dien-3-one (88257-21-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 53 percent / CuCl / tetrahydrofuran 2: 75 percent / p-TSA View Scheme

(5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → 11-[4-(dimethyl-phosphinoyl)-phenyl]-17-hydroxy-13-methyl-17-prop-1-ynyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one

Conditions	Yield
Multi-step reaction with 4 steps 1: 53 percent / CuCl / tetrahydrofuran 2: 75 percent / p-TSA 3: 60 percent / NaH 4: Pd(OAc)2; dppb; i-Pr2NEt / microwave irradiation View Scheme

(5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → trifluoro-methanesulfonic acid 4-(17-hydroxy-13-methyl-3-oxo-17-prop-1-ynyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)-phenyl ester (167846-17-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 53 percent / CuCl / tetrahydrofuran 2: 75 percent / p-TSA 3: 60 percent / NaH View Scheme

(5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → [4-(17-hydroxy-13-methyl-3-oxo-17-prop-1-ynyl-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)-phenyl]-phosphonic acid diethyl ester

Conditions	Yield
Multi-step reaction with 4 steps 1: 53 percent / CuCl / tetrahydrofuran 2: 75 percent / p-TSA 3: 60 percent / NaH 4: Pd(OAc)2; dppb; i-Pr2NEt / microwave irradiation View Scheme

(5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → 11-[4-(diphenyl-phosphinoyl)-phenyl]-17-hydroxy-13-methyl-17-prop-1-ynyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one

Conditions	Yield
Multi-step reaction with 4 steps 1: 53 percent / CuCl / tetrahydrofuran 2: 75 percent / p-TSA 3: 60 percent / NaH 4: Pd(OAc)2; dppb; i-Pr2NEt / microwave irradiation View Scheme

1-bromo-2,6-difluoro4-methoxybenzene + (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → C30H34F2O4

Conditions	Yield
Stage #1: 1-bromo-2,6-difluoro4-methoxybenzene With iodine; magnesium In tetrahydrofuran for 0.25h; Heating; Stage #2: (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol With copper(l) iodide In tetrahydrofuran at 0℃; Further stages.;

1-bromo-2,5-difluoro-4-methoxybenzene + (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → C30H34F2O4

Conditions	Yield
Stage #1: 1-bromo-2,5-difluoro-4-methoxybenzene With iodine; magnesium In tetrahydrofuran for 0.25h; Heating; Stage #2: (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol With copper(l) iodide In tetrahydrofuran at 0℃; Further stages.;

C10H10BrClO (918823-90-2) + (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → C33H39ClO4

Conditions	Yield
Stage #1: C10H10BrClO With iodine; magnesium In tetrahydrofuran for 0.25h; Heating; Stage #2: (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol With copper(l) iodide In tetrahydrofuran at 0℃; Further stages.;

2-bromo-1-fluoro-3,5-dimethoxybenzene (206860-47-1) + (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → C31H37FO5

Conditions	Yield
Stage #1: 2-bromo-1-fluoro-3,5-dimethoxybenzene With iodine; magnesium In tetrahydrofuran for 0.25h; Heating; Stage #2: (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol With copper(l) iodide In tetrahydrofuran at 0℃; Further stages.;

1-bromo-4-methoxy-benzene (104-92-7) + (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → C30H36O4

Conditions	Yield
Stage #1: 1-bromo-4-methoxy-benzene With iodine; magnesium In tetrahydrofuran for 0.25h; Heating; Stage #2: (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol With copper(l) iodide In tetrahydrofuran at 0℃; Further stages.;

4-Bromodiphenyl ether (101-55-3) + (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → C35H38O4

Conditions	Yield
Stage #1: 4-Bromodiphenyl ether With iodine; magnesium In tetrahydrofuran for 0.25h; Heating; Stage #2: (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol With copper(l) iodide In tetrahydrofuran at 0℃; Further stages.;

(4-bromophenyl)thioanisole (104-95-0) + (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → C30H36O3S

Conditions	Yield
Stage #1: (4-bromophenyl)thioanisole With iodine; magnesium In tetrahydrofuran for 0.25h; Heating; Stage #2: (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol With copper(l) iodide In tetrahydrofuran at 0℃; Further stages.;

4-bromo-3-methylanisole (27060-75-9) + (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → C31H38O4

Conditions	Yield
Stage #1: 4-bromo-3-methylanisole With iodine; magnesium In tetrahydrofuran for 0.25h; Heating; Stage #2: (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol With copper(l) iodide In tetrahydrofuran at 0℃; Further stages.;

5-bromo-2-methoxy-1,3-dimethylbenzene (14804-38-7) + (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → C32H40O4

Conditions	Yield
Stage #1: 5-bromo-2-methoxy-1,3-dimethylbenzene With iodine; magnesium In tetrahydrofuran for 0.25h; Heating; Stage #2: (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol With copper(l) iodide In tetrahydrofuran at 0℃; Further stages.;

4-bromo-4'-methoxylbiphenyl (58743-83-2) + (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → C36H40O4

Conditions	Yield
Stage #1: 4-bromo-4'-methoxylbiphenyl With iodine; magnesium In tetrahydrofuran for 0.25h; Heating; Stage #2: (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol With copper(l) iodide In tetrahydrofuran at 0℃; Further stages.;

2-bromo-1,3,5-trimethoxybenzene (1131-40-4) + (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → C32H40O6

Conditions	Yield
Stage #1: 2-bromo-1,3,5-trimethoxybenzene With iodine; magnesium In tetrahydrofuran for 0.25h; Heating; Stage #2: (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol With copper(l) iodide In tetrahydrofuran at 0℃; Further stages.;

4-Bromo-2-methylphenol (2362-12-1) + (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → C30H36O4

Conditions	Yield
Stage #1: 4-Bromo-2-methylphenol With iodine; magnesium In tetrahydrofuran for 0.25h; Heating; Stage #2: (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol With copper(l) iodide In tetrahydrofuran at 0℃; Further stages.;

2-methyl-4-bromoanisole (14804-31-0) + (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3) → C31H38O4

Conditions	Yield
Stage #1: 2-methyl-4-bromoanisole With iodine; magnesium In tetrahydrofuran for 0.25h; Heating; Stage #2: (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol With copper(l) iodide In tetrahydrofuran at 0℃; Further stages.;

Upstream product

• 4529-04-8 1-propynyl lithium 
• 39931-88-9 (5'R,10'R,13'S)-13'-methyl-1',2',6',7',8',12',13',14',15',16'-decahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one 
• 84371-69-7 (8S,13S,14S,17S)-13-methyl-17-(prop-1-yn-1-yl)-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol 
• 639520-94-8 (5'R,10'R,13'S,16'R)-13',16'-dimethyl-1',2',6',7',8',12',13',14',15'-nonahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one 
• 16466-97-0 1-propynylmagnesium bromide 
• 5571-36-8 ethylene deltenone 

Downstream Products

• 934415-53-9 C₃₄H₄₄O₆ 
• 329971-39-3 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N-methyl-N-cyclohexylamino)phenyl]-17α-(1-propynyl)-9(10)-estrene 
• 639520-75-5 tert-butyl 4-((5R,11R,13S,17S)-5,17-dihydroxy-13-methyl-17-prop-1-ynyl-1,2,4,5,6,7,8,11,12,13,14,15,16,17-tetradecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-11-yl)phenyl(methyl)carbamate 
• 88256-81-9 (8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-11-(4-phenoxyphenyl)-17-(prop-1-yn-1-yl)-6,7,8,11,12,13,14,15,16,17-decahydro-7H-cyclopenta[a]phenanthrone-3(2H)-one 

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