Water → HCID 15838157, compound

HRID 1603323Notes

Reaction equation

HRID 1603323 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)-estr4-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 31 of diethyl ether, the organic phase is dried and concentrated by evaporation after washing with sodium bicarbonate solution. The residue is chromatographed on silica gel, and 84.4 g of 7α-(5-acetoxypentyl)-estr-4-ene-3,17-dione is obtained as oil.

Workup

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

Sources & evidence

ORD record
ord-a4863172d91d41a89f2caa4f9660c842
Source dataset
uspto-grants-1999_11
Patent number
US05986115

Reaction notes

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