반응 #3185

ord-78b65606c5ee45768c20fb14a7e7de91

반응 방정식

CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCC(=O)O)[C@@]4(C)CC[C@@H]32)C1
3β-acetoxy-5-cholenic acid
O=C(Cl)C(=O)Cl
oxalyl chloride
→
CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCC(=O)Cl)[C@@]4(C)CC[C@@H]32)C1
3β-acetoxy-5-cholenic acid chloride

반응물

CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4CC[C@H]([C@H](C)CCC(=O)O)[C@@]4(C)CC[C@@H]32)C1
3β-acetoxy-5-cholenic acid
O=C(Cl)C(=O)Cl
oxalyl chloride

시약

없음

용매

ClCCl
dichloromethane

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    농축concentrated in vacuo

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05733899uspto-grants-1998_03