HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Formaldehyde → 17beta-Hydroxy-17alpha-methyl-4-(phenylthiomethyl)androsta-4,15-dien-3-one

HRID 274303
Notes
Print preview

Reaction equation

HRID 274303 reaction equation
[OH:1][C@@:2]1([CH3:22])[CH:7]=[CH:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:21])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.[C:23]1([SH:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH2:30]=O>N(CCO)(CCO)CCO>[OH:1][C@@:2]1([CH3:22])[CH:7]=[CH:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C:11](=[C:12]([CH2:30][S:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:13](=[O:21])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 712Formaldehyde2×HCID 7969Thiophenol2×HCID 1567913617beta-Hydroxy-17alpha-methylandrosta-4,15-dien-3-one

Product 1

HCID 1567914117beta-Hydroxy-17alpha-methyl-4-(phenylthiomethyl)androsta-4,15-dien-3-one

Reagents, catalysts & solvents 1

HCID 7618TriethanolamineSolvent

Procedure

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).

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ff640dddd972414dbaa189aa2ba81f45
Source dataset
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05389624

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes