反応 #3185

ord-78b65606c5ee45768c20fb14a7e7de91

反応方程式

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

反応物

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

試薬

なし

溶媒

ClCCl
dichloromethane

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    濃縮concentrated in vacuo

実験手順

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.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US05733899uspto-grants-1998_03