Acetic Anhydride → HCID 86738163, compound

HRID 1660113Notes

Reaction equation

HRID 1660113 reaction equation
[C:1]([C@:3]1([OH:24])[CH:9]=[CH:8][C@H:7]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH2:5][CH3:6])[C@@H:18]1[C:13](=[CH:14][C:15](=[O:23])[CH2:16][C@@H:17]1[OH:22])[CH2:12][CH2:11]3)#[CH:2].[C:25](OC(=O)C)(=[O:27])[CH3:26]>N1C=CC=CC=1>[C:25]([O:22][C@@H:17]1[C@H:18]2[C:13]([CH2:12][CH2:11][C@@H:10]3[C@@H:19]2[CH2:20][CH2:21][C@@:4]2([CH2:5][CH3:6])[C@H:7]3[CH:8]=[CH:9][C@:3]2([C:1]#[CH:2])[OH:24])=[CH:14][C:15](=[O:23])[CH2:16]1)(=[O:27])[CH3:26]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86738164HCID 86738164, compound

Product 1

HCID 86738163HCID 86738163, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

200 mg of 17α-ethynyl-1α,17-dihydroxy-18-methyl-4,15-estradien-3-one is dissolved in 10 ml of pyridine and combined under ice-cooling dropwise with 3 m of acetic anhydride. The solution is then allowed to warm up and agitated at room temperature overnight. Thereafter the reaction mixture is stirred into ice water, the precipitated, oily-crystalline product is vacuum-filtered, taken up in ethyl acetate, washed neutral, dried over Na2SO4, and concentrated to dryness under vacuum. The remaining residue is crystallized from ether/hexane, thus obtaining 165 mg of 1α-acetoxy-17α-ethynyl-17-hydroxy-18-methyl-4,15-estradien-3-one, mp 123°-126° C.

Workup

  1. temperatureto warm up
  2. filtrationthe precipitated, oily-crystalline product is vacuum-filtered
  3. washwashed neutral
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness under vacuum
  6. customThe remaining residue is crystallized from ether/hexane

Sources & evidence

ORD record
ord-f74b82c4e4344e75b4bd9860c9c7df3b
Source dataset
uspto-grants-1981_12
Patent number
US04307088

Reaction notes

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