Diethyl Ether → HCID 13917420, compound

HRID 986200Notes

Reaction equation

HRID 986200 reaction equation
[C:1]([O:4][C@@H:5]1[C@@:27]2([CH3:28])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:29])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:22])[CH2:18][CH2:19][CH2:20][OH:21])[CH2:8][C@@H:7]([O:30][C:31](=[O:33])[CH3:32])[CH2:6]1)(=[O:3])[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCOCC>C(Cl)Cl>[C:1]([O:4][C@@H:5]1[C@@:27]2([CH3:28])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:29])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:22])[CH2:18][CH2:19][CH:20]=[O:21])[CH2:8][C@@H:7]([O:30][C:31](=[O:33])[CH3:32])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 13243603HCID 13243603, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 13917420HCID 13917420, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 650 mg (1.42 mmols) of 1α,3β-diacetoxychol-5-en-24-ol in 35 ml of methylene chloride was added 750 mg (3.48 mmols) of pyridinium chlorochromate, and the resulting mixture was stirred at room temperature for 2 hours. Subsequently, 100 ml of ether was added to the mixture and the solution was eluted through a column filled with 15 g of Florisil to give 550 mg of 1α,3β-diacetoxychol-5-en-24-al (Compound B).

Workup

  1. washthe solution was eluted through a column
  2. additionfilled with 15 g of Florisil

Sources & evidence

ORD record
ord-731d707b3f63408a989f4cc40ad2751a
Source dataset
uspto-grants-1987_12
Patent number
US04711881

Reaction notes

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