반응 #1164383

ord-38544423709142e38776a2862590a572

반응 방정식

C#C[C@@]1(O)CC[C@H]2[C@@H]3CCC4=C(CC=C(OC)C4)[C@H]3CC[C@@]21CCC
13β-n-propyl-3-methoxy-17β-ethynyl-gona-2,5(10)-dien-17 -ol
O
water
Cl
hydrochloric acid
O
water
CO
methanol
→
C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21CCC
title compound
수율 33.6%
C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21CCC
13β-n-Propyl-17α-ethynyl-17β-hydroxy-gon-4en-3-one
수율 33.6%

반응물

C#C[C@@]1(O)CC[C@H]2[C@@H]3CCC4=C(CC=C(OC)C4)[C@H]3CC[C@@]21CCC
13β-n-propyl-3-methoxy-17β-ethynyl-gona-2,5(10)-dien-17 -ol
O
water
Cl
hydrochloric acid
O
water
CO
methanol

시약

없음

용매

CCOCC
ether

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    workup.DISSOLUTIONuntil the solid dissolves
  2. 2
    기타purify by recrystallization from cyclohexane

실험 절차

Shake 13β-n-propyl-3-methoxy-17β-ethynyl-gona-2,5(10)-dien-17 -ol (0.31 g.) with a solution prepared by mixing concentrated hydrochloric acid (0.81 cc.), water (0.54 cc.) and methanol (12.15 cc.), until the solid dissolves. After addition of water, work up with ether, purify by recrystallization from cyclohexane to obtain the title compound (0.1 g.), m.p. 149°-50.5°; ultraviolet absorption peak at 240 mμ (ε15,700); infrared absorption peaks at 2.99, 3.06, 6.04, 6.16 μ.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US03959322uspto-grants-1976_05