Oxalyl chloride → 3beta-Acetoxy-5-cholenic acid chloride

HRID 863415Notes

Reaction equation

HRID 863415 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[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:21])[CH2:16][CH2:17][C:18](O)=[O:19])[CH2:6]1)(=[O:3])[CH3:2].C(Cl)(=O)C([Cl:34])=O>ClCCl>[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[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:21])[CH2:16][CH2:17][C:18]([Cl:34])=[O:19])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 111017913beta-Acetoxy-5-cholenic acid

Product 1

HCID 129533373beta-Acetoxy-5-cholenic acid chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3β-acetoxy-5-cholenic acid (50.0 g, 118 mmole) in dry dichloromethane (200 ml) was added dropwise oxalyl chloride (30 ml, 448 mmole). The solution was stirred at room temperature for one hour and then concentrated in vacuo to obtain 3β-acetoxy-5-cholenic acid chloride 331. 1H NMR (400 MHz, CDCl3) δ: 0.70 (3H, s, 18--CH3), 0.95 (3H, d, 21--CH3), 1.05 (3H, s, 19--CH3), 2.04 (3H, s, --OCOCH3), 4.60 (1H, m, 3α-H), 5.38 (1H, m, 6-H). Compound 331 was used in the following step without purification.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d5268be02a164516bad0cb3bf3d66993
Source dataset
uspto-grants-1998_02
Patent number
US05721226

Reaction notes

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