تفاعل #3185

ord-78b65606c5ee45768c20fb14a7e7de91

معادلة التفاعل

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

المتفاعلات

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

الكواشف

لا شيء

المذيبات

ClCCl
dichloromethane

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    تركيزconcentrated in vacuo

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05733899uspto-grants-1998_03