반응 #70363

ord-5b12658c6c454522b0b3d55dc323d513

반응 방정식

O
H2O
C=C1C[C@@H]2[C@H](CC[C@@]3(C)[C@H]2CC24OCCOC23OCCO4)[C@@]2(C)CCCCC12
17,17-bis(ethylendioxy)-6-methyleneandrostane
Cc1ccc(S(=O)(=O)O)cc1
pTSA
O=C([O-])O.[Na+]
NaHCO3
→
C=C1C[C@@H]2[C@H](CC[C@]3(C)C(=O)CC[C@@H]23)[C@@]2(C)CCC(=O)CC12
title compound
수율 87.0%
C=C1C[C@@H]2[C@H](CC[C@]3(C)C(=O)CC[C@@H]23)[C@@]2(C)CCC(=O)CC12
6-Methyleneandrostane-3,17-dione
수율 87.0%

반응물

O
H2O
C=C1C[C@@H]2[C@H](CC[C@@]3(C)[C@H]2CC24OCCOC23OCCO4)[C@@]2(C)CCCCC12
17,17-bis(ethylendioxy)-6-methyleneandrostane
Cc1ccc(S(=O)(=O)O)cc1
pTSA
O=C([O-])O.[Na+]
NaHCO3

시약

없음

용매

CC(C)=O
acetone
CC(C)=O
acetone

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타was evaporated
  2. 2
    추출The aqueous suspension was extracted with CH2Cl2 (3×)
  3. 3
    세척The combined organic extracts were washed with H2O
  4. 4
    건조dried over Na2SO4
  5. 5
    기타evaporated to dryness

실험 절차

A solution of 3,3:17,17-bis(ethylendioxy)-6-methyleneandrostane (1.05 g) and pTSA.H2O (2.46 g) in acetone (105 mL) was stirred at room temperature for 3 h. The solution was neutralized by addition of 5% aqueous NaHCO3 and acetone was evaporated. The aqueous suspension was extracted with CH2Cl2 (3×). The combined organic extracts were washed with H2O, dried over Na2SO4 and evaporated to dryness to give the title compound II-ac in 87% yield. 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 4.85 (1H, m), 4.50 (1H, m), 2.63-1.02 (20H, m), 0.92 (3H, s), 0.86 (3H, s).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08536160B2uspto-grants-2013_09