Water → HCID 15838157, compound

HRID 1595971Notes

Reaction equation

HRID 1595971 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[C@H:18]([CH2:19][CH2:20][C:21](=[O:25])[CH:22]=2)[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][CH2:16]2)([CH3:14])[C:12](=[O:26])[CH2:11][CH2:10]1.[C:27](OC(=O)C)(=[O:29])[CH3:28].O>N1C=CC=CC=1.C(OCC)C>[C:27]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[C@H:18]([CH2:19][CH2:20][C:21](=[O:25])[CH:22]=2)[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][CH2:16]2)([CH3:14])[C:12](=[O:26])[CH2:11][CH2:10]1)(=[O:29])[CH3:28]

Participants

6

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 158381567a-(5-Hydroxypentyl)-estr-4-ene-3,17-dione

Product 1

HCID 15838157HCID 15838157, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 94 g of crude 7α-(5-hydroxypentyl)-estr-4-ene-3,17-dione in 620 ml of pyridine is slowly mixed with 310 ml of acetic anhydride and stirred for 2 hours at 25° C. Then, it is slowly mixed with 116 ml of water while being cooled with ice, diluted with 3 l of diethyl ether, and, after washing with sodium bicarbonate solution, the organic phase is dried and concentrated by evaporation. The residue is chromatographed on silica gel, and 84.4 g of 7α-(5-acetoxypentyl)-estr-4-ene-3,17-dione is obtained as an oil.

Workup

  1. temperaturewhile being cooled with ice
  2. washafter washing with sodium bicarbonate solution
  3. customthe organic phase is dried
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-62e91cc880d14e86b65fce2cd03f1c9c
Source dataset
uspto-grants-2001_09
Patent number
US06288051B1

Reaction notes

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