반응 #361485

ord-ff640dddd972414dbaa189aa2ba81f45

반응 방정식

C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C=C[C@]2(C)O
17β-hydroxy-17α-methylandrosta-4,15-dien-3-one
Sc1ccccc1
thiophenol
C=O
formaldehyde
Sc1ccccc1
thiophenol
C=O
formaldehyde
→
C[C@]12CCC(=O)C(CSc3ccccc3)=C1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C=C[C@]2(C)O
17β-hydroxy-17α-methyl-4-(phenylthiomethyl)androsta-4,15-dien-3-one

반응물

—
ice water
C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C=C[C@]2(C)O
17β-hydroxy-17α-methylandrosta-4,15-dien-3-one
Sc1ccccc1
thiophenol
C=O
formaldehyde
Sc1ccccc1
thiophenol
C=O
formaldehyde

시약

없음

용매

OCCN(CCO)CCO
triethanolamine

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    세척washed with water
  2. 2
    기타dried
  3. 3
    농축concentrated under vacuum

실험 절차

Under argon, 9.2 g of 17β-hydroxy-17α-methylandrosta-4,15-dien-3-one in 80 ml of triethanolamine is allowed to react at 110° C. with 2.1 ml of thiophenol and 2.1 ml of aqueous formaldehyde solution (37%). After 5 hours and another 18 hours, respectively 2.1 ml of thiophenol and 2.1 ml of formaldehyde solution are added. In total, the reaction mixture is stirred for 32 hours and subsequently introduced into ice/water. The precipitated product is suctioned off, washed with water, taken up in methylene chloride, dried, and concentrated under vacuum. After chromatographing the crude product on silica gel with a hexane-ethyl acetate gradient, 7.9 g of 17β-hydroxy-17α-methyl-4-(phenylthiomethyl)androsta-4,15-dien-3-one is obtained, mp 146.8° C. (from acetone/hexane).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05389624uspto-grants-1995_02