Thionyl Chloride → HCID 22803791, compound

HRID 839522Notes

Reaction equation

HRID 839522 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH2:23][O:24][C:25](=[O:27])[CH3:26])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@:11]3(O)[CH2:12][CH2:13][C@@H:14]2[O:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:6]1)(=[O:3])[CH3:2].S(Cl)(Cl)=O>N1C=CC=CC=1>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH2:23][O:24][C:25](=[O:27])[CH3:26])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C:11]3=[CH:12][CH2:13][C@@H:14]2[O:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22803789HCID 22803789, compound

Product 1

HCID 22803791HCID 22803791, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 140 mg of 3β,19-diacetoxy-14β-hydroxy-17β-pivaloxy-5α-androstane in 7.0 ml of pyridine was added 0.14 ml of thionyl chloride. The mixture was left to stand under nitrogen for 40 minutes whereupon it was poured into 70 ml of an ice-water mixture. Extraction with ether followed by washing of the ethereal phase with water and evaporation at reduced pressure gave 3β,19-diacetoxy-17β-pivaloxy-5α-androst-14-ene as a resinous material which was used as the starting material in the reaction described in the following example.

Workup

  1. waitThe mixture was left
  2. extractionExtraction with ether
  3. washby washing of the ethereal phase with water and evaporation at reduced pressure

Sources & evidence

ORD record
ord-05752d0fea1a4031a74490ff429af877
Source dataset
uspto-grants-1978_06
Patent number
US04096142

Reaction notes

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