Water → HCID 22800265, compound

HRID 371696Notes

Reaction equation

HRID 371696 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH2:23][OH:24])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[O:25][C:26](=[O:28])[CH3:27])[CH2:6]1)(=[O:3])[CH3:2].[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1.O>N1C=CC=CC=1>[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35]([O:24][CH2:23][C@@:20]23[C@@H:19]4[C@H:10]([C@H:11]5[C@@:15]([CH2:17][CH2:18]4)([CH3:16])[C@@H:14]([O:25][C:26](=[O:28])[CH3:27])[CH2:13][CH2:12]5)[CH2:9][CH:8]=[C:7]2[CH2:6][C@@H:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:22][CH2:21]3)(=[O:37])=[O:36])=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14630436HCID 14630436, compound

Product 1

HCID 22800265HCID 22800265, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3β,17β-diacetoxy-19-hydroxyandrost-5-ene (14.4g) in pyridine (370ml) at 25° is added p-toluenesulfonyl chloride (38.1g) and the solution is left at 25° for 4 days. Water is then added, and the mixture is extracted with ethyl acetate, and the organic extract is washed successively with water, 5% aqueous hydrochloric acid, 5% aqueous sodium bicarbonate and water, and then dried (Na2SO4) and evaporated in vacuo. The residue is crystallized from methylene chloride-hexane to give the compound of this Example (11), mp. 135°-137°; mass spectrum m/e 484, 372, 312.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. extractionthe organic extract
  3. washis washed successively with water, 5% aqueous hydrochloric acid, 5% aqueous sodium bicarbonate and water
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customThe residue is crystallized from methylene chloride-hexane
  7. customto give the compound of this Example (11), mp. 135°-137°

Sources & evidence

ORD record
ord-4b0409617b8340a8809c0a033331e18c
Source dataset
uspto-grants-1978_05
Patent number
US04087461

Reaction notes

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