HCID 70466764, compound → HCID 70466802, compound

HRID 279857Notes

Reaction equation

HRID 279857 reaction equation
[C:1]([O:4][CH:5]1[C@@H:22]2[CH2:23][C@@H:21]2[C@@:20]2([CH3:24])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[OH:25])[CH2:6]1)(=[O:3])[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl.C(OCC)C>[C:1]([O:4][CH:5]1[C@@H:22]2[CH2:23][C@@H:21]2[C@@:20]2([CH3:24])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:25])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 70466764HCID 70466764, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 70466802HCID 70466802, compoundYield 103.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 6.8 g of 3-acetoxy-1α,2α-methylene-5α-androstan-17β-ol in 68 ml of dichloromethane is combined with 10.2 g of pyridinium chlorochromate and stirred for one hour at room temperature, then diluted with diethyl ether, washed with water, and dried. Evaporation yields 7.0 g of 3-acetoxy-1α,2α-methylene-5α-androstan-17-one.

Workup

  1. washwashed with water
  2. customdried
  3. customEvaporation

Sources & evidence

ORD record
ord-e67fb3ed9e1c435dbb3840429b65a395
Source dataset
uspto-grants-1986_05
Patent number
US04587235

Reaction notes

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