Pyridine → 17beta-Tetrahydropyranyloxy-5alpha-androstan-4-one

HRID 27333Notes

Reaction equation

HRID 27333 reaction equation
N1C=CC=CC=1.ClCCl.[O:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[O:16][C@H:17]1[CH2:22][CH2:21][C@H:20]2[C@H:23]3[C@H:33]([CH2:34][CH2:35][C@:18]12[CH3:19])[C@:31]1([CH3:32])[C@H:26]([C@@H:27]([OH:36])[CH2:28][CH2:29][CH2:30]1)[CH2:25][CH2:24]3>O.[O-2].[O-2].[O-2].[Cr+6]>[O:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[O:16][C@H:17]1[CH2:22][CH2:21][C@H:20]2[C@H:23]3[C@H:33]([CH2:34][CH2:35][C@:18]12[CH3:19])[C@:31]1([CH3:32])[C@H:26]([C:27](=[O:36])[CH2:28][CH2:29][CH2:30]1)[CH2:25][CH2:24]3

Participants

6

Reactant 3

HCID 1049PyridineHCID 6344Dichloromethane2×HCID 1534189617beta-Tetrahydropyranyloxy-4beta-hydroxy-5alpha-androstane

Product 1

HCID 1534189717beta-Tetrahydropyranyloxy-5alpha-androstan-4-one

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent

Procedure

To 0.42 ml. of dry pyridine and 6.3 ml. of dry dichloromethane was slowly added 0.264 g. of chromium trioxide and the mixture was stirred for 15 min. at room temperature. To the mixture was added a solution of 175 mg. of the product of Step D in 0.7 ml. of dichloromethane and the resulting mixture was stirred for 20 min. at room temperature. The mixture was diluted with water, extracted with ethyl ether, and washed with 2.5 N sodium hydroxide, water, and brine. The mixture was then dried and evaporated to a clear oil.

Workup

  1. additionTo the mixture was added a solution of 175 mg
  2. extractionextracted with ethyl ether
  3. washwashed with 2.5 N sodium hydroxide, water, and brine
  4. customThe mixture was then dried
  5. customevaporated to a clear oil

Sources & evidence

ORD record
ord-7a6bd310f23044b3a8a42f553dc70e79
Source dataset
uspto-grants-1980_09
Patent number
US04220775

Reaction notes

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