Water → HCID 13578831, compound

HRID 1285313Notes

Reaction equation

HRID 1285313 reaction equation
[C:1]1([S:7](Cl)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([C@:13]1(O)[C:18](=[CH2:19])[CH2:17][C@H:16]2[C@H:20]3[C:30](=[CH:31][CH2:32][C@:14]12[CH3:15])[C@:28]1([CH3:29])[C:23](=[CH:24][C:25](=[O:33])[CH2:26][CH2:27]1)[CH2:22][CH2:21]3)(=[O:12])[CH3:11].C(N(CC)CC)C.O>C(Cl)Cl>[C:1]1([S:7]([CH2:19][C:18]2[CH2:17][C@@H:16]3[C@:14]([CH3:15])([CH2:32][CH:31]=[C:30]4[C@H:20]3[CH2:21][CH2:22][C:23]3[C@:28]4([CH3:29])[CH2:27][CH2:26][C:25](=[O:33])[CH:24]=3)[C:13]=2[C:10](=[O:12])[CH3:11])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 4190003Benzenesulfinyl chlorideHCID 13578828HCID 13578828, compound

Product 1

HCID 13578831HCID 13578831, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of phenylsulfinylchloride (2.5N, 1.4 ml) in methylene chloride was added dropwise over a period of 1.5 hrs to a solution of 17-acetyl-17β-hydroxy-16-methyleneandrost-4,9(11)-dien-3-one (VA, Example 12, 1 g) in methylene chloride (10 ml) containing triethylamine (0.82 ml) previously cooled equal to 31 55°. Water was added to the reaction mixture, the organic phase separated, washed with water, dried over sodium sulfate, and concentrated under reduced pressure to a partially crystalline substance. Crystallization from toluene gives the title compound, m.p. 160°-163°; NMR (CDCl3) 0.87, 1.36, 2.11, 4.03, 5.50 and 5.75 δ.

Workup

  1. customthe organic phase separated
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure to a partially crystalline substance
  5. customCrystallization from toluene

Sources & evidence

ORD record
ord-82212ced9b1149af9cd078bc1ed88b61
Source dataset
uspto-grants-1986_01
Patent number
US04567001

Reaction notes

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