Hydrogen Peroxide → HCID 12992472, compound

HRID 2085910Notes

Reaction equation

HRID 2085910 reaction equation
[OH:1][C@H:2]1[CH2:7][C@@H:6]2[CH2:8][C@:5]32[C@H:9]2[C@H:18]([CH2:19][CH2:20][C@:3]13[CH3:4])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]2.OO.FC1C(=[O:43])CC[C@H]2C=1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@@]31C[C@H]3C[C@H]2O.[OH-].[Na+]>CO.O.ClCCl>[O:43]1[C:12]23[C@H:17]([CH2:16][CH2:15][C:14](=[O:21])[CH:13]12)[C@@H:18]1[C@H:9]([C@:5]24[CH2:8][C@H:6]2[CH2:7][C@H:2]([OH:1])[C@:3]4([CH2:20][CH2:19]1)[CH3:4])[CH2:10][CH2:11]3

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 15432774HCID 15432774, compoundHCID 69888577HCID 69888577, compound

Product 1

HCID 12992472HCID 12992472, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

17β-Hydroxy-14α,15α-methylene-estr-4-ene-3-one (2 g) was dissolved in 50 ml of methanol and treated at 10° C. with hydrogen peroxide solution (35%). While stirring, 5 ml of a 10 sodium hydroxide solution was added and the stirring was continued for 3 hours. The reaction solution is mixed with 50 ml of dichloromethane and 25 ml of water and the organic phase is removed, washed with semi-concentrated thiosulfate solution, dried and evaporated to dryness. The residue obtained consists of a mixture of 4α,5α- and 4β,5β epoxides and is used in the subsequent step without further purification.

Workup

  1. customthe organic phase is removed
  2. washwashed with semi-concentrated thiosulfate solution
  3. customdried
  4. customevaporated to dryness
  5. customThe residue obtained
  6. customis used in the subsequent step without further purification

Sources & evidence

ORD record
ord-305d8608dbcf4d2e880d0044ee7bc393
Source dataset
uspto-grants-2004_04
Patent number
US06723715B1

Reaction notes

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