(E)-2-{4-[4-methyl-3-(methylethyl)pentylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}acetic acid

Base Information

Chemical Name:(E)-2-{4-[4-methyl-3-(methylethyl)pentylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}acetic acid
CAS No.:663601-16-9
Molecular Formula:C₂₃H₃₂O₅
Molecular Weight:388.504
Hs Code.:

Synonyms:(E)-2-{4-[4-methyl-3-(methylethyl)pentylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}acetic acid

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Chemical Property of (E)-2-{4-[4-methyl-3-(methylethyl)pentylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}acetic acid

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Technology Process of (E)-2-{4-[4-methyl-3-(methylethyl)pentylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}acetic acid

There total 19 articles about (E)-2-{4-[4-methyl-3-(methylethyl)pentylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}acetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 663601-14-7
(E)-3-[4-methyl-3-(methylethyl)pentylidene]-5-(2-oxoethyl)-5-[(phenylmethoxy)methyl]-4,5-dihydrofuran-2-one

: 663601-16-9
(E)-2-{4-[4-methyl-3-(methylethyl)pentylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}acetic acid

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tert-butyl alcohol; at 20 ℃;
DOI:10.1021/jm030454h

Reference yield:

: 17325-85-8
(2S)-3-(benzyloxy)propane-1,2-diol

: 663601-16-9
(E)-2-{4-[4-methyl-3-(methylethyl)pentylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}acetic acid

Guidance literature:: Multi-step reaction with 19 steps

1.1: imidazole / CH₂Cl₂ / 1.42 h / 20 °C

1.2: CH₂Cl₂; dimethylformamide / 20 °C

2.1: 46.9 g / pyridinium chlorochromate; 4A molecular sieves / CH₂Cl₂ / 2 h / Heating

3.1: tetrahydrofuran / 0 - 20 °C

4.1: BH₃*SMe₂ / tetrahydrofuran / -78 - 20 °C

4.2: 31.7 g / pyridinium chlorochromate; 4A molecular sieves / CH₂Cl₂ / 48 h

5.1: diisobutylaluminum hydride / tetrahydrofuran; toluene / -78 °C

6.1: Dowex 50WX₈-200; aq. AcOH / tetrahydrofuran

7.1: TBAF / tetrahydrofuran / 0 - 20 °C

8.1: 1,3-dicyclohexylcarbodiimide; dichloroacetic acid; DMSO / 16 h

9.1: t-BuOK / tetrahydrofuran / 0.5 h

9.2: 240 mg / tetrahydrofuran

10.1: BH₃*SMe₂ / tetrahydrofuran / 17 h / -78 - 0 °C

10.2: 56 percent / NaBO₃*H₂O / tetrahydrofuran / 2 h / 0 - 20 °C

11.1: NaH / tetrahydrofuran / Heating

11.2: 77 percent / Bu₄NI / 72 h / Heating

12.1: 74 percent / aq. HCl / tetrahydrofuran / 0 - 20 °C

13.1: 84 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; 4A molecular sieves / CH₂Cl₂; acetonitrile / 0 - 20 °C

14.1: LDA / tetrahydrofuran; heptane; ethylbenzene / 2 h / -78 °C

14.2: tetrahydrofuran; heptane; ethylbenzene / -78 °C

15.1: Et₃N / CH₂Cl₂ / 2.5 h / 0 - 20 °C

16.1: 600 mg / DBU / CH₂Cl₂ / 3 h / 20 °C

17.1: 76 percent / aq. 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 2.5 h

18.1: (COCl)2; DMSO / CH₂Cl₂ / 1 h / -78 °C

19.1: 2-methyl-2-buten; NaClO₂; aq. NaH₂PO₄ / 2-methyl-propan-2-ol / 20 °C

With 1H-imidazole; hydrogenchloride; dichloro-acetic acid; sodium chlorite; sodium dihydrogenphosphate; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; oxalyl dichloride; dimethylsulfide borane complex; 4 A molecular sieve; DOWEX 50WX₈-200; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; dichloromethane; ethylbenzene; toluene; acetonitrile; tert-butyl alcohol; 18.1: Swern oxidation;
DOI:10.1021/jm030454h

Reference yield:

: 335393-68-5
3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-1-(phenylmethoxy)aceton

: 663601-16-9
(E)-2-{4-[4-methyl-3-(methylethyl)pentylidene]-5-oxo-2-[(phenylmethoxy)methyl]-2-2,3-dihydrofuryl}acetic acid

Guidance literature:: Multi-step reaction with 17 steps

1.1: tetrahydrofuran / 0 - 20 °C

2.1: BH₃*SMe₂ / tetrahydrofuran / -78 - 20 °C

2.2: 31.7 g / pyridinium chlorochromate; 4A molecular sieves / CH₂Cl₂ / 48 h

3.1: diisobutylaluminum hydride / tetrahydrofuran; toluene / -78 °C

4.1: Dowex 50WX₈-200; aq. AcOH / tetrahydrofuran

5.1: TBAF / tetrahydrofuran / 0 - 20 °C

6.1: 1,3-dicyclohexylcarbodiimide; dichloroacetic acid; DMSO / 16 h

7.1: t-BuOK / tetrahydrofuran / 0.5 h

7.2: 240 mg / tetrahydrofuran

8.1: BH₃*SMe₂ / tetrahydrofuran / 17 h / -78 - 0 °C

8.2: 56 percent / NaBO₃*H₂O / tetrahydrofuran / 2 h / 0 - 20 °C

9.1: NaH / tetrahydrofuran / Heating

9.2: 77 percent / Bu₄NI / 72 h / Heating

10.1: 74 percent / aq. HCl / tetrahydrofuran / 0 - 20 °C

11.1: 84 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; 4A molecular sieves / CH₂Cl₂; acetonitrile / 0 - 20 °C

12.1: LDA / tetrahydrofuran; heptane; ethylbenzene / 2 h / -78 °C

12.2: tetrahydrofuran; heptane; ethylbenzene / -78 °C

13.1: Et₃N / CH₂Cl₂ / 2.5 h / 0 - 20 °C

14.1: 600 mg / DBU / CH₂Cl₂ / 3 h / 20 °C

15.1: 76 percent / aq. 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 2.5 h

16.1: (COCl)2; DMSO / CH₂Cl₂ / 1 h / -78 °C

17.1: 2-methyl-2-buten; NaClO₂; aq. NaH₂PO₄ / 2-methyl-propan-2-ol / 20 °C

With hydrogenchloride; dichloro-acetic acid; sodium chlorite; sodium dihydrogenphosphate; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; oxalyl dichloride; dimethylsulfide borane complex; 4 A molecular sieve; DOWEX 50WX₈-200; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; dichloromethane; ethylbenzene; toluene; acetonitrile; tert-butyl alcohol; 16.1: Swern oxidation;
DOI:10.1021/jm030454h