Acetic Acid → 7a-(5-Hydroxypentyl)-estr-4-ene-3,17-dione

HRID 650328Notes

Reaction equation

HRID 650328 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C@@H:14]1[CH2:31][C:30]2[C@H:25]([CH2:26][CH2:27][C:28](=[O:32])[CH:29]=2)[C@@H:24]2[C@@H:15]1[C@H:16]1[C@@:20]([CH2:22][CH2:23]2)([CH3:21])[C:19](=[O:33])[CH2:18][CH2:17]1)(C(C)(C)C)(C)C.C(O)(=O)C>CO.O>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C@@H:14]1[CH2:31][C:30]2[C@H:25]([CH2:26][CH2:27][C:28](=[O:32])[CH:29]=2)[C@@H:24]2[C@@H:15]1[C@H:16]1[C@@:20]([CH2:22][CH2:23]2)([CH3:21])[C:19](=[O:33])[CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 229418117alpha-(5-Tert-butyldimethylsilyloxypentyl)-estr-4-ene-3,17-dione

Product 1

HCID 158381567a-(5-Hydroxypentyl)-estr-4-ene-3,17-dioneYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 125.4 g of 7α-(5-tert-butyldimethylsilyloxypentyl)-estr-4-ene-3,17-dione in 625 ml of methanol and 347 ml of water is stirred with 694 ml of glacial acetic acid for 2.5 hours at 50° C. After the concentration by evaporation at 60° C. in a vacuum, 94.1 g of crude 7α-(5-hydroxypentyl)-estr-4-ene-3,17-dione is obtained as oil.

Workup

  1. concentrationAfter the concentration
  2. customby evaporation at 60° C. in a vacuum

Sources & evidence

ORD record
ord-11652617edc246d0a48c70c96623fb5f
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

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