Thiophenol → HCID 69874424, compound

HRID 49411Notes

Reaction equation

HRID 49411 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:8][C@H:7]2[CH2:9][C@@:6]32[C@H:10]2[C@H:19]([CH2:20][CH2:21][C@:4]13[CH3:5])[C@@H:18]1[C:13](=[CH:14][C:15](=[O:22])[CH2:16][CH2:17]1)[CH2:12][C@H:11]2[CH3:23].[CH2:24](N(CC)CC)C.[C:31]1([SH:37])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[OH-].[K+]>C=O.C(O)C>[OH:1][CH2:2][C@@H:3]1[CH2:8][C@H:7]2[CH2:9][C@@:6]32[C@H:10]2[C@H:19]([CH2:20][CH2:21][C@:4]13[CH3:5])[C@@H:18]1[C:13](=[C:14]([CH2:24][S:37][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:15](=[O:22])[CH2:16][CH2:17]1)[CH2:12][C@H:11]2[CH3:23]

Participants

7

Reactant 4

HCID 7969ThiophenolHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 9796915(7alpha,14beta,15beta,17alpha)-17-(Hydroxymethyl)-7-methyl-14,15-methyleneestr-4-en-3-one

Product 1

HCID 69874424HCID 69874424, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 712FormaldehydeSolvent

Procedure

i)—A solution of (7α,14β,15β,17α)-17-(hydroxymethyl)-7-methyl-14,15-methyleneestr-4-en-3-one (Example 1, 0.40 g) in a mixture of formaldehyde (37 wt. % solution in water, 0.24 ml), triethylamine (0.288 ml), thiophenol (0.276 ml) and ethanol (0.721 ml) was stirred at room temperature overnight. The reaction mixture was poured into a aqueous solution of potassium hydroxide (0.5 M) and the product was extracted into ethyl acetate. The combined organic phases were washed with a aqueous solution of potassium hydroxide (0.5 M) and brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography afforded (7α,14β,15β,17α)-17-(hydroxymethyl)-7-methyl-4-[(phenylthio)methyl]-14,15-methyleneestr-4-en-3-one (0.13 g).

Workup

  1. extractionthe product was extracted into ethyl acetate
  2. washThe combined organic phases were washed with a aqueous solution of potassium hydroxide (0.5 M) and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4e4fb220f8e74d9c9c832a67bcad8100
Source dataset
uspto-grants-2004_03
Patent number
US06706700B2

Reaction notes

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