Water → HCID 86736873, compound

HRID 1701448Notes

Reaction equation

HRID 1701448 reaction equation
[I:1][CH2:2][C:3]([O:5][C@H:6]1[CH2:25][C@@:24]2([CH3:26])[C@@H:17]([CH2:18][CH2:19][C@@H:20]2[C:21](=[O:23])[CH3:22])[C@H:16]2[C@H:7]1[C@:8]1([CH3:32])[C@@H:13]([CH2:14][CH2:15]2)[CH2:12][C@H:11](OS(C)(=O)=O)[CH2:10][CH2:9]1)=[O:4].O>C(O)(C)(C)C>[I:1][CH2:2][C:3]([O:5][C@H:6]1[CH2:25][C@@:24]2([CH3:26])[C@@H:17]([CH2:18][CH2:19][C@@H:20]2[C:21](=[O:23])[CH3:22])[C@H:16]2[C@H:7]1[C@:8]1([CH3:32])[C@@H:13]([CH2:14][CH2:15]2)[CH2:12][CH:11]=[CH:10][CH2:9]1)=[O:4]

Participants

4

Reactant 2

HCID 962WaterHCID 86736874HCID 86736874, compound

Product 1

HCID 86736873HCID 86736873, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of 11β-iodoacetoxy-3α-methanesulphonyloxy-5α-pregnan-20-one (22.2 g) in t-butanol (950 ml) containing water (500 ml) was treated with powdered silica gel (44 g) and refluxed with stirring for 75 minutes. The cooled mixture was filtered and the filtrate was evaporated to small bulk and diluted with water. The precipitated solid was collected by filtration and recrystallized from aqueous methanol to afford title compound (12.77 g). A sample recrystallized from acetone-petroleum ether had m.p. 127°-129°, [α]D +100.5°.

Workup

  1. additionwas treated with powdered silica gel (44 g)
  2. temperaturerefluxed
  3. filtrationThe cooled mixture was filtered
  4. customthe filtrate was evaporated to small bulk
  5. additiondiluted with water
  6. filtrationThe precipitated solid was collected by filtration
  7. customrecrystallized from aqueous methanol

Sources & evidence

ORD record
ord-1706c84c25e347ccb4b54f70b59dcc0b
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

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