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

HRID 3089Notes

Reaction equation

HRID 3089 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-78b65606c5ee45768c20fb14a7e7de91
Source dataset
uspto-grants-1998_03
Patent number
US05733899

Reaction notes

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