Oxalyl chloride → HCID 54351697, compound

HRID 2039411Notes

Reaction equation

[C:1]([OH:26])(=O)[CH2:2][CH2:3][C@H:4]([C@@H:6]1[C@:23]2([CH3:24])[C@H:9]([C@H:10]3[C@H:20]([CH2:21][CH2:22]2)[C@:18]2([CH3:19])[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:12][CH2:11]3)[CH2:8][CH2:7]1)[CH3:5].C(Cl)(=O)C([Cl:30])=O>C(Cl)Cl>[C:1]([Cl:30])(=[O:26])[CH2:2][CH2:3][C@H:4]([C@@H:6]1[C@:23]2([CH3:24])[C@H:9]([C@H:10]3[C@H:20]([CH2:21][CH2:22]2)[C@:18]2([CH3:19])[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:12][CH2:11]3)[CH2:8][CH2:7]1)[CH3:5]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 0.5 g (1.39 mmol) of 5β-cholanic acid (Aldrich), 0.4 mL (4.6 mmol) of oxalyl chloride, and 10 mL of methylene chloride was heated in a sealed reaction vessel at 60° C. for 15 minutes. The volatiles were distilled off to give 5β-cholanoyl chloride as a colorless solid in quantitative yield. m.p. 104-106° C. 1H NMR (CDCl3, 500 MHz): δ 2.94 (m, 1H), 2.83 (m, 1H), 2.00-0.67 (m, 37H).

Workup

distillationThe volatiles were distilled off

Sources & evidence

ORD record: ord-500083ab6a344a1997446d8df4951bd9
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580384B2

Reaction notes

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