Sodium Acetate → HCID 22817078, compound

HRID 894496Notes

Reaction equation

HRID 894496 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+].[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[O:23][C@@H:24]1[CH2:46][CH2:45][C@@:44]2([CH3:47])[C@H:26]([CH2:27][CH2:28][C@@H:29]3[C@@H:43]2[CH2:42][CH2:41][C@@:40]2([CH3:48])[C@H:30]3[CH2:31][CH2:32][C@@H:33]2[C@H:34]([CH3:39])[CH2:35][CH2:36][CH2:37][OH:38])[CH2:25]1>ClCCl>[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[O:23][C@@H:24]1[CH2:46][CH2:45][C@@:44]2([CH3:47])[C@H:26]([CH2:27][CH2:28][C@@H:29]3[C@@H:43]2[CH2:42][CH2:41][C@@:40]2([CH3:48])[C@H:30]3[CH2:31][CH2:32][C@@H:33]2[C@H:34]([CH3:39])[CH2:35][CH2:36][CH:37]=[O:38])[CH2:25]1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 12767260HCID 12767260, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 22817078HCID 22817078, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension comprising a mixture of 221 mg of pyridinium chlorochromate (C5H5N+HCrO3Cl-) and 8.3 mg of sodium acetate in 1 ml of dichloromethane was prepared. To the suspension, a solution of 221 mg of 3α-(2-tetrahydropyranyloxy)-24-hydroxy-5β-cholane in 4 ml of dichloromethane was added at one time in an argon stream under stirring. After stirring for 3 hours, the supernatant of the reaction mixture was separated by decantation, and the precipitate was washed with dichloromethane three times. The supernatant was combined with the washings, passed through a short column with silica gel (4 g). The eluate with dichloromethane was concentrated under vacuum. 3α-(2-Tetrahydropyranyloxy)-24-oxo-5β-cholane (177 mg) was obtained as a colorless oily substance.

Workup

  1. customwas prepared
  2. stirringAfter stirring for 3 hours
  3. customthe supernatant of the reaction mixture was separated by decantation
  4. washthe precipitate was washed with dichloromethane three times
  5. concentrationThe eluate with dichloromethane was concentrated under vacuum

Sources & evidence

ORD record
ord-09dc7aaaa7f549bb99305b3f27a7cec6
Source dataset
uspto-grants-1981_08
Patent number
US04284577

Reaction notes

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