Acetic Anhydride → HCID 13025346, compound

HRID 1757934Notes

Reaction equation

HRID 1757934 reaction equation
[OH:1][C@@H:2]1[C@H:8]2[C@H:9]3[C@H:18]([C:19](=[CH2:21])[CH2:20][C@:5]2([CH2:6][CH3:7])[C:4](=[O:23])[CH2:3]1)[C@@H:17]1[C:12](=[CH:13][C:14](=[O:22])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3.[C:24](OC(=O)C)(=[O:26])[CH3:25]>N1C=CC=CC=1>[C:24]([O:1][C@@H:2]1[C@H:8]2[C@H:9]3[C@H:18]([C:19](=[CH2:21])[CH2:20][C@:5]2([CH2:6][CH3:7])[C:4](=[O:23])[CH2:3]1)[C@@H:17]1[C:12](=[CH:13][C:14](=[O:22])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)(=[O:26])[CH3:25]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 13025344HCID 13025344, compound

Product 1

HCID 13025346HCID 13025346, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.2 g of 15α-hydroxy-18-methyl-11-methylene-4-estrene-3,17-dione is reacted in 10 ml of pyridine with 2.5 ml of acetic anhydride under argon at room temperature within 2 hours. The solution is introduced into ice/water. The thus-precipitated crude product is vacuum-filtered, dissolved in ethyl acetate, and dried. Chromatography of the crude product on silica gel with 0-20% acetone/hexane yields 1.7 g of 15α-acetoxy-18-methyl-11-methylene-4-estrene-3,17-dione, mp 176.3° C.

Workup

  1. customThe thus-precipitated crude product
  2. filtrationis vacuum-filtered
  3. dissolutiondissolved in ethyl acetate
  4. customdried

Sources & evidence

ORD record
ord-eacea4f8217b4f35b840b60781539308
Source dataset
uspto-grants-1983_02
Patent number
US04371529

Reaction notes

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