182699-77-0

Basic information

• Product Name: 3A,4,5,7A-TETRAHYDRO-3,6-DIMETHYLBENZOFURAN-2(3H)-ONE
• Synonyms: FEMA 4140;3A,4,5,7A-TETRAHYDRO-3,6-DIMETHYLBENZOFURAN-2(3H)-ONE;WINE LACTONE;winelactone,(3S,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one
• CAS NO: 182699-77-0
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22
• Mol File: 182699-77-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 286.3 ºC at 760 mmHg
• Flash Point: 115.5 ºC
• Appearance: /
• Density: 1.042 g/cm³
• Vapor Pressure: 0.00266mmHg at 25°C
• Refractive Index: 1.484
• CAS DataBase Reference: 3A,4,5,7A-TETRAHYDRO-3,6-DIMETHYLBENZOFURAN-2(3H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3A,4,5,7A-TETRAHYDRO-3,6-DIMETHYLBENZOFURAN-2(3H)-ONE(182699-77-0)
• EPA Substance Registry System: 3A,4,5,7A-TETRAHYDRO-3,6-DIMETHYLBENZOFURAN-2(3H)-ONE(182699-77-0)

Safety Data

• Hazardous Substances Data: 182699-77-0(Hazardous Substances Data)

Usage

Uses

Wine Lactone is a terpenoid used in wine flavour. A key odorant in wine.

InChI:InChI=1/C10H14O2/c1-6-3-4-8-7(2)10(11)12-9(8)5-6/h5,7-9H,3-4H2,1-2H3

Synthetic route

(3aS,7aS)-6-methyl-3-methylene-3a,4,5,7a-tetrahydrobenzofuran-2(3H)-one (477717-60-5) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0) + (+)-(3aR,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-79-2)

Conditions	Yield
With [NH2Me2][{RuCl((S)-segphos)}2(μ-Cl)3]; hydrogen In 1,4-dioxane at 40℃; under 15001.5 Torr; for 6h; Inert atmosphere; Autoclave; diastereoselective reaction;	A n/a B 99%
With [NH2Me2][{RuCl((R)-H8-binap)}2(μ-Cl)3]; hydrogen In 1,4-dioxane at 30℃; under 15001.5 Torr; for 16h; Inert atmosphere; Autoclave; diastereoselective reaction;	A 69% B n/a
With sodium tetrahydroborate In ethanol at 20℃; for 1.5h; Product distribution; Further Variations:; Reagents;	A 5 % Chromat. B 92 % Chromat.
With magnesium In methanol at 20℃; for 3h;

(+)-(3aS,7aR)-2,3,3a,4,5,7a-hexahydro-6-methylbenzofuran-2(3H)-one (263163-03-7) + methyl iodide (74-88-4) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
Stage #1: (+)-(3aS,7aR)-2,3,3a,4,5,7a-hexahydro-6-methylbenzofuran-2(3H)-one With n-butyllithium; diisopropylamine In tetrahydrofuran at -20 - 0℃; for 1h; Inert atmosphere; Stage #2: methyl iodide With 1,3-dimethyl-2-imidazolidinone In tetrahydrofuran at 0 - 20℃; for 5h; Inert atmosphere;	90%
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1.5h; Alkylation;	79%

(3S,3aS,6R,7R,7aR)-(3a,4,5,6,7,7a)-hexahydro-3,6-dimethylbenzofuran-2(3H)-one (416864-79-4) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 5h;	76%

(2RS)-2-<(1R)-4-methylcyclohex-3-enyl>propanoic acid (287720-48-3) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0) + (+)-(3aR,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-79-2)

Conditions	Yield
With tert.-butylhydroperoxide; dipyridinium dichromate; Celite In N,N-dimethyl-formamide at 30℃; for 12h;
With tert.-butylhydroperoxide; dipyridinium dichromate; Celite In benzene at 30℃; for 12h;

(3S,3aS,7aS)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-81-6) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
With hydrogenchloride; sodium hydroxide 1.) water/MeOH, 80 deg C, 2 h, 2.) water/MeOH, 80 deg C, 2 h; Yield given. Multistep reaction;

(3R,3aS,7aS)-3,6-dimethyl-3,3a,4,5-tetrahydrobenzofuran-2(7aH)-one (182699-83-8) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
With hydrogenchloride; sodium hydroxide 1.) water/MeOH, 80 deg C, 2 h, 2.) water/MeOH, 80 deg C, 2 h; Yield given. Multistep reaction;

2-((1R,4R)-4-Methyl-cyclohex-2-enyl)-propionic acid (416864-77-2) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: FeCl3; NaI / acetonitrile / 2.5 h / Heating 2: 76 percent / DBU / tetrahydrofuran / 5 h / 20 °C View Scheme

(-)-(3aS,7R,7aR)-hexahydro-7-iodo-benzo[b]furan-2-one (160224-76-0) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: 82 percent / DBU / tetrahydrofuran / 3 h / Heating 2: 87 percent / CuBr*Me2S / tetrahydrofuran / 12 h / -10 °C 3: 60 percent / KI; I2; NaHCO3 / tetrahydrofuran; H2O / 2 h / 20 °C 4: 92 percent / DBU / tetrahydrofuran / 2 h / Heating 5: 79 percent / LDA / tetrahydrofuran / 1.5 h / -78 °C View Scheme

methyl (+)-(S)-(cyclohex-2-enyl)acetate (263163-00-4) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions

Yield

Multi-step reaction with 7 steps 1: 95 percent / NaOH / 1 h / 120 °C 2: 66 percent / KI; I2; NaHCO3 / H2O / 5 h / 20 °C 3: 82 percent / DBU / tetrahydrofuran / 3 h / Heating 4: 87 percent / CuBr*Me2S / tetrahydrofuran / 12 h / -10 °C 5: 60 percent / KI; I2; NaHCO3 / tetrahydrofuran; H2O / 2 h / 20 °C 6: 92 percent / DBU / tetrahydrofuran / 2 h / Heating 7: 79 percent / LDA / tetrahydrofuran / 1.5 h / -78 °C View Scheme

dimethyl 2-(cyclohex-2-en-1-yl)propanedioate (34939-28-1, 78601-28-2, 138258-79-4, 78601-26-0) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions

Yield

Multi-step reaction with 8 steps 1: 74 percent / NaCl / H2O; dimethylsulfoxide / 24 h / 160 °C 2: 95 percent / NaOH / 1 h / 120 °C 3: 66 percent / KI; I2; NaHCO3 / H2O / 5 h / 20 °C 4: 82 percent / DBU / tetrahydrofuran / 3 h / Heating 5: 87 percent / CuBr*Me2S / tetrahydrofuran / 12 h / -10 °C 6: 60 percent / KI; I2; NaHCO3 / tetrahydrofuran; H2O / 2 h / 20 °C 7: 92 percent / DBU / tetrahydrofuran / 2 h / Heating 8: 79 percent / LDA / tetrahydrofuran / 1.5 h / -78 °C View Scheme

(3aS,7aR)-(+)-2,3,3a,4,5,7a-hexahydrobenzofuran-2-one (145414-43-3) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / CuBr*Me2S / tetrahydrofuran / 12 h / -10 °C 2: 60 percent / KI; I2; NaHCO3 / tetrahydrofuran; H2O / 2 h / 20 °C 3: 92 percent / DBU / tetrahydrofuran / 2 h / Heating 4: 79 percent / LDA / tetrahydrofuran / 1.5 h / -78 °C View Scheme

(+)-(S)-cyclohex-2-enylacetic acid (137174-05-1) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
Multi-step reaction with 6 steps 1: 66 percent / KI; I2; NaHCO3 / H2O / 5 h / 20 °C 2: 82 percent / DBU / tetrahydrofuran / 3 h / Heating 3: 87 percent / CuBr*Me2S / tetrahydrofuran / 12 h / -10 °C 4: 60 percent / KI; I2; NaHCO3 / tetrahydrofuran; H2O / 2 h / 20 °C 5: 92 percent / DBU / tetrahydrofuran / 2 h / Heating 6: 79 percent / LDA / tetrahydrofuran / 1.5 h / -78 °C View Scheme

(2S,4R/4S)-(4-methylcyclohex-2-enyl)acetic acid → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 60 percent / KI; I2; NaHCO3 / tetrahydrofuran; H2O / 2 h / 20 °C 2: 92 percent / DBU / tetrahydrofuran / 2 h / Heating 3: 79 percent / LDA / tetrahydrofuran / 1.5 h / -78 °C View Scheme

(-)-(3aS,6R,7R,7aR)-3a,4,5,6,7,7a-hexahydro-7-iodo-6-methylbenzofuran-2(3H)-one (263163-02-6) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / DBU / tetrahydrofuran / 2 h / Heating 2: 79 percent / LDA / tetrahydrofuran / 1.5 h / -78 °C View Scheme

3-methylcyclohexen-2-one (1193-18-6) + (PhMe2Si)2CuLi → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: 50 percent / BuLi,(i-Pr)2NH / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 2 h / -20 °C 2: NaBH4, CaCl2 / propan-2-ol / 2 h / 0 °C 3: NaOH / H2O; methanol / 12 h / Ambient temperature 4: N,N'-dicyclohexylcarbodiimide / benzene / 8 h / 25 °C 5: 1.) NaOH, 2.) HCl / 1.) water/MeOH, 80 deg C, 2 h, 2.) water/MeOH, 80 deg C, 2 h View Scheme
Multi-step reaction with 5 steps 1: 50 percent / BuLi,(i-Pr)2NH / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 2 h / -20 °C 2: NaBH4, CaCl2 / propan-2-ol / 2 h / 0 °C 3: NaOH / H2O; methanol / 12 h / Ambient temperature 4: N,N'-dicyclohexylcarbodiimide / benzene / 8 h / 25 °C 5: 1.) NaOH, 2.) HCl / 1.) water/MeOH, 80 deg C, 2 h, 2.) water/MeOH, 80 deg C, 2 h View Scheme

D-limonene (5989-27-5) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) 9-BBN, 2.) 6M NaOH, 30percent H2O2 / 1.) THF, 2.) EtOH, 1 h, 50 deg C 2: 39 percent / PDC / dimethylformamide / 12 h / 20 °C 3: pyridinium dichromate, t-BuOOH, celite / benzene / 12 h / 30 °C View Scheme

(2RS)-2-<(1R)-4-methylcyclohex-3-enyl>propanol (287720-47-2) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 39 percent / PDC / dimethylformamide / 12 h / 20 °C 2: pyridinium dichromate, t-BuOOH, celite / benzene / 12 h / 30 °C View Scheme

6-(1'-methylcarbonyl-ethyl)-3-methyl-2-cyclohexenone (83037-73-4) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: NaBH4, CaCl2 / propan-2-ol / 2 h / 0 °C 2: NaOH / H2O; methanol / 12 h / Ambient temperature 3: N,N'-dicyclohexylcarbodiimide / benzene / 8 h / 25 °C 4: 1.) NaOH, 2.) HCl / 1.) water/MeOH, 80 deg C, 2 h, 2.) water/MeOH, 80 deg C, 2 h View Scheme
Multi-step reaction with 4 steps 1: NaBH4, CaCl2 / propan-2-ol / 2 h / 0 °C 2: NaOH / H2O; methanol / 12 h / Ambient temperature 3: N,N'-dicyclohexylcarbodiimide / benzene / 8 h / 25 °C 4: 1.) NaOH, 2.) HCl / 1.) water/MeOH, 80 deg C, 2 h, 2.) water/MeOH, 80 deg C, 2 h View Scheme

methyl 2-((S)-4-methylcyclohex-3-enyl)propanoate → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: pyridinium dichromate, t-BuOOH, celite / benzene / 24 h / 30 °C 2: NaBH4, CaCl2 / propan-2-ol / 2 h / 0 °C 3: NaOH / H2O; methanol / 12 h / Ambient temperature 4: N,N'-dicyclohexylcarbodiimide / benzene / 8 h / 25 °C 5: 1.) NaOH, 2.) HCl / 1.) water/MeOH, 80 deg C, 2 h, 2.) water/MeOH, 80 deg C, 2 h View Scheme

2-(2-Hydroxy-4-methyl-cyclohex-3-enyl)-propionic acid methyl ester (182489-56-1) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaOH / H2O; methanol / 12 h / Ambient temperature 2: N,N'-dicyclohexylcarbodiimide / benzene / 8 h / 25 °C 3: 1.) NaOH, 2.) HCl / 1.) water/MeOH, 80 deg C, 2 h, 2.) water/MeOH, 80 deg C, 2 h View Scheme
Multi-step reaction with 3 steps 1: NaOH / H2O; methanol / 12 h / Ambient temperature 2: N,N'-dicyclohexylcarbodiimide / benzene / 8 h / 25 °C 3: 1.) NaOH, 2.) HCl / 1.) water/MeOH, 80 deg C, 2 h, 2.) water/MeOH, 80 deg C, 2 h View Scheme

2-((1R,2S)-2-Hydroxy-4-methyl-cyclohex-3-enyl)-propionic acid methyl ester → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaOH / H2O; methanol / 12 h / Ambient temperature 2: N,N'-dicyclohexylcarbodiimide / benzene / 8 h / 25 °C 3: 1.) NaOH, 2.) HCl / 1.) water/MeOH, 80 deg C, 2 h, 2.) water/MeOH, 80 deg C, 2 h View Scheme

2-((1S,2S)-2-Hydroxy-4-methyl-cyclohex-3-enyl)-propionic acid → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N'-dicyclohexylcarbodiimide / benzene / 8 h / 25 °C 2: 1.) NaOH, 2.) HCl / 1.) water/MeOH, 80 deg C, 2 h, 2.) water/MeOH, 80 deg C, 2 h View Scheme
Multi-step reaction with 2 steps 1: N,N'-dicyclohexylcarbodiimide / benzene / 8 h / 25 °C 2: 1.) NaOH, 2.) HCl / 1.) water/MeOH, 80 deg C, 2 h, 2.) water/MeOH, 80 deg C, 2 h View Scheme

2-((1R,2S)-2-Hydroxy-4-methyl-cyclohex-3-enyl)-propionic acid → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N'-dicyclohexylcarbodiimide / benzene / 8 h / 25 °C 2: 1.) NaOH, 2.) HCl / 1.) water/MeOH, 80 deg C, 2 h, 2.) water/MeOH, 80 deg C, 2 h View Scheme

2-((R)-4-Methyl-2-oxo-cyclohex-3-enyl)-propionic acid methyl ester → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: NaBH4, CaCl2 / propan-2-ol / 2 h / 0 °C 2: NaOH / H2O; methanol / 12 h / Ambient temperature 3: N,N'-dicyclohexylcarbodiimide / benzene / 8 h / 25 °C 4: 1.) NaOH, 2.) HCl / 1.) water/MeOH, 80 deg C, 2 h, 2.) water/MeOH, 80 deg C, 2 h View Scheme

methyl iodide (74-88-4) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
Stage #1: (+)-(3aS,7aR)-2,3,3a,4,5,7a-hexahydro-6-methylbenzofuran-2(3H)-one With n-butyllithium; diisopropylamine In tetrahydrofuran at 0℃; Stage #2: methyl iodide In tetrahydrofuran for 0.333333h; Stage #3: With water In tetrahydrofuran

methyl 3-(methoxycarbonyl)-2-methyl-4-oxopentanoate (35493-66-4) → epi-wine lactone (57743-63-2) + (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0) + (3R,3aR,7aS)-3,3a,4,5-tetrahydro-3,6-dimethylbenzofuran-2(7aH)-one (182699-78-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 0.5 h / 40 °C 1.2: 3 h / 40 °C 2.1: 1,4-diaza-bicyclo[2.2.2]octane; formic acid; ((R,R)-Ts-DENEB)RuCl / methanol / 70 h / 60 °C View Scheme
Multi-step reaction with 3 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 0.5 h / 40 °C 1.2: 3 h / 40 °C 2.1: sodium hydroxide / water / 1 h / 0 - 20 °C 3.1: 1,4-diaza-bicyclo[2.2.2]octane; formic acid; ((R,R)-Ts-DENEB)RuCl / methanol / 20 h / 60 °C View Scheme

C10H14O3 (1415228-03-3) → epi-wine lactone (57743-63-2) + (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0) + (3R,3aR,7aS)-3,3a,4,5-tetrahydro-3,6-dimethylbenzofuran-2(7aH)-one (182699-78-1)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; formic acid; ((R,R)-Ts-DENEB)RuCl In methanol at 60℃; for 20h; Reagent/catalyst;	A n/a B n/a C n/a

6-(1'-methylcarbonyl-ethyl)-3-methyl-2-cyclohexenone (83037-73-4) → epi-wine lactone (57743-63-2) + (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0) + (3R,3aR,7aS)-3,3a,4,5-tetrahydro-3,6-dimethylbenzofuran-2(7aH)-one (182699-78-1)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; formic acid; ((R,R)-Ts-DENEB)RuCl In methanol at 60℃; for 70h; Reagent/catalyst;	A n/a B n/a C n/a

2-(4-methyl-2-oxocyclohex-3-en-1-yl)acetic acid (20778-34-1) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: formic acid; RuCl((R,R)-O-HT-TIPPsDPEN); 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 16 h / 60 - 80 °C / Inert atmosphere 2.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1 h / -20 - 0 °C / Inert atmosphere 2.2: 5 h / 0 - 20 °C / Inert atmosphere View Scheme

2-(4-methyl-2-oxocyclohex-3-en-1-yl)acetic acid (20778-34-1) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0) + (+)-(3aR,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-79-2)

Conditions

Yield

Multi-step reaction with 3 steps 1.1: formic acid; RuCl((R,R)-O-HT-TIPPsDPEN); 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 16 h / 60 - 80 °C / Inert atmosphere 2.1: sodium hydride; oxalic acid diethyl ester / tetrahydrofuran; mineral oil; ethanol / 4 h / 0 - 20 °C / Inert atmosphere 2.2: 0.25 h / 0 °C 3.1: [NH2Me2][{RuCl((S)-segphos)}2(μ-Cl)3]; hydrogen / 1,4-dioxane / 6 h / 40 °C / 15001.5 Torr / Inert atmosphere; Autoclave View Scheme

(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0) → (3R,4S,8S)-3,9-epoxy-p-menth-1-ene (74410-10-9)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 1h;	82%

(-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0) → (+)-(3aR,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-79-2)

Conditions	Yield
Stage #1: (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Deprotonation; Stage #2: With t-butyl malonate In tetrahydrofuran at -78℃; for 0.666667h; Reprotonation, Epimerization;	61%

Upstream product

• 182489-56-1 2-(2-Hydroxy-4-methyl-cyclohex-3-enyl)-propionic acid methyl ester 
• 83037-73-4 6-(1'-methylcarbonyl-ethyl)-3-methyl-2-cyclohexenone 
• 287720-47-2 (2RS)-2-<(1R)-4-methylcyclohex-3-enyl>propanol 
• 5989-27-5 D-limonene 
• 1193-18-6 3-methylcyclohexen-2-one 
• 263163-02-6 (-)-(3aS,6R,7R,7aR)-3a,4,5,6,7,7a-hexahydro-7-iodo-6-methylbenzofuran-2(3H)-one 
• 137174-05-1 (+)-(S)-cyclohex-2-enylacetic acid 
• 145414-43-3 (3aS,7aR)-(+)-2,3,3a,4,5,7a-hexahydrobenzofuran-2-one 
• 34939-28-1 dimethyl 2-(cyclohex-2-en-1-yl)propanedioate 
• 263163-00-4 methyl (+)-(S)-(cyclohex-2-enyl)acetate 
• 160224-76-0 (-)-(3aS,7R,7aR)-hexahydro-7-iodo-benzo[b]furan-2-one 
• 416864-77-2 2-((1R,4R)-4-Methyl-cyclohex-2-enyl)-propionic acid 
• 477717-60-5 (3aS,7aS)-6-methyl-3-methylene-3a,4,5,7a-tetrahydrobenzofuran-2(3H)-one 
• 416864-79-4 (3S,3aS,6R,7R,7aR)-(3a,4,5,6,7,7a)-hexahydro-3,6-dimethylbenzofuran-2(3H)-one 

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