Acetic Anhydride → HCID 22789120, compound

HRID 1606299Notes

Reaction equation

HRID 1606299 reaction equation
[S:1]([O:5][C:6]1[C:23]2[C@@H:22]3[C@@H:13]([C@H:14]4[C@@:18]([CH2:20][CH2:21]3)([CH3:19])[C@@H:17]([OH:24])[CH2:16][CH2:15]4)[CH2:12][CH2:11][C:10]=2[CH:9]=[C:8]([O:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:7]=1)([CH3:4])(=[O:3])=[O:2].[C:30](OC(=O)C)(=[O:32])[CH3:31]>N1C=CC=CC=1>[S:1]([O:5][C:6]1[C:23]2[C@@H:22]3[C@@H:13]([C@H:14]4[C@@:18]([CH2:20][CH2:21]3)([CH3:19])[C@@H:17]([O:24][C:30](=[O:32])[CH3:31])[CH2:16][CH2:15]4)[CH2:12][CH2:11][C:10]=2[CH:9]=[C:8]([O:25][S:26]([CH3:29])(=[O:27])=[O:28])[CH:7]=1)([CH3:4])(=[O:3])=[O:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86733252HCID 86733252, compound

Product 1

HCID 22789120HCID 22789120, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 200 mg. of 1,3-bis(mesyloxy)-8α-estra-1,3,5(10)-trien-17β-ol in 3 ml. of pyridine is combined with 2 ml. of acetic anhydride and allowed to stand at room temperature for 3 days. Then, the mixture is introduced into ice water, extracted with methylene chloride, washed with water, dried, and evaporated. The residue (180 mg.) is purified by layer chromatography, thus obtaining 150 mg. of 1,3-bis(mesyloxy)-17β-acetoxy-8α-estra- 1,3,5(100-triene.

Workup

  1. extractionextracted with methylene chloride
  2. washwashed with water
  3. customdried
  4. customevaporated
  5. customThe residue (180 mg.) is purified by layer chromatography
  6. customthus obtaining 150 mg

Sources & evidence

ORD record
ord-ea45331926c746d49b1d08d6ae41ecfd
Source dataset
uspto-grants-1976_04
Patent number
US03951959

Reaction notes

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