Sulfuric Acid → HCID 70634285, compound

HRID 596979Notes

Reaction equation

HRID 596979 reaction equation
[C:1]([O:4][C@H:5]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:30])[C@H:11]3[C@H:12]3[CH2:31][C@H:13]3[C:14]2=[C:15]([O:18][C:19](=[O:21])[CH3:20])[CH:16]=[O:17])[CH2:6]1)(=[O:3])[CH3:2].[Li].S(=O)(=O)(O)O>O1CCCC1>[OH:17][CH2:16][C:15]([O:18][C:19](=[O:21])[CH3:20])=[C:14]1[C@:22]2([CH3:30])[C@H:11]([C@H:10]3[C@H:25]([CH2:24][CH2:23]2)[C@:26]2([CH3:29])[C:7]([CH2:6][C@@H:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:28][CH2:27]2)=[CH:8][CH2:9]3)[C@H:12]2[CH2:31][C@@H:13]12

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 3028194LithiumHCID 88818465HCID 88818465, compound

Product 1

HCID 70634285HCID 70634285, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.5 g. of 3β,20-diacetoxy-15α,16α-methylene-5,17(20)-pregnadien-21-al is mixed in 65 ml. of tetrahydrofuran with 6.5 g. of lithium tri-tert.-butoxyalanate and agitated for 30 minutes at room temperature. The mixture is then stirred into ice water, acidified with dilute sulfuric acid, and extracted with methylene chloride. After drying and evaporation, 6.5 g. of crude 21-hydroxy-3β,20-diacetoxy-15α,16α-methylene-5,17(20)-pregnadiene is obtained.

Workup

  1. extractionextracted with methylene chloride
  2. customAfter drying
  3. customevaporation, 6.5 g

Sources & evidence

ORD record
ord-e6fd981e0fbc4ec2a6f75e0432a17294
Source dataset
uspto-grants-1977_03
Patent number
US04012510

Reaction notes

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