Acetic Anhydride → 17alpha-Acetoxy-3-methoxy-1,3,5(10),15-estratetraene

HRID 328210Notes

Reaction equation

HRID 328210 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C@H:12]([OH:21])[CH:11]=[CH:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>N1C=CC=CC=1>[C:22]([O:21][C@@H:12]1[CH:11]=[CH:10][C@H:9]2[C@H:8]3[C@H:17]([CH2:16][CH2:15][C@:13]12[CH3:14])[C:18]1[CH:19]=[CH:20][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH2:6][CH2:7]3)(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 227968373-Methoxy-1,3,5(10),15-estratetraen-17alpha-ol

Product 1

HCID 2279683417alpha-Acetoxy-3-methoxy-1,3,5(10),15-estratetraene

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

200 mg. of 3-methoxy-1,3,5(10),15-estratetraen-17α-ol is agitated for 3 hours in 2.5 ml. of pyridine with 0.5 ml. of acetic anhydride. After the product has been worked up as described in Example 4 and purified by preparative layer chromatography (eluent: hexane/ethyl acetate = 7 : 3), 170 mg. of 17α-acetoxy-3-methoxy-1,3,5(10),15-estratetraene is isolated as an oily product.

Workup

  1. custompurified by preparative layer chromatography (eluent: hexane/ethyl acetate = 7 : 3), 170 mg

Sources & evidence

ORD record
ord-6a5b5773a7b942a09c345d3be209d397
Source dataset
uspto-grants-1977_04
Patent number
US04016269

Reaction notes

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