Water → HCID 68866327, compound

HRID 543651Notes

Reaction equation

HRID 543651 reaction equation
[CH3:1][C:2]1[CH2:3][C@H:4]2[C@:17]([CH3:20])([CH2:18][CH:19]=1)[C@@H:16]1[C@H:7]([C@H:8]3[C@@:12]([CH2:14][CH2:15]1)([CH3:13])[C@@H:11]([OH:21])[CH2:10][CH2:9]3)[CH2:6][CH2:5]2.O>CC(C)=O>[CH3:1][C:2]1[CH2:3][C@H:4]2[C@:17]([CH3:20])([CH2:18][CH:19]=1)[C@@H:16]1[C@H:7]([C@H:8]3[C@@:12]([CH2:14][CH2:15]1)([CH3:13])[C:11](=[O:21])[CH2:10][CH2:9]3)[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 962WaterHCID 22857985639-55-0

Product 1

HCID 68866327HCID 68866327, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Kiliani's reagent (100 ml) was added slowly to a solution of 3-methyl-5α-androst-2-en-17β-ol (43 g) in acetone (170 ml). When the addition was complete, water was added to give a precipitate, which was filtered off. The product was redissolved in acetone and water was again added. The precipitate was filtered off, washed with water and dried to give 3-methyl-5α-androst-2-en-17-one (35.7 g). A sample was recrystallised from ether-light petroleum (40°-60°) and from ether to give pure material, m.p. 124°-126°; [α]D +141° (c 0.48 in EtOH).

Workup

  1. additionWhen the addition
  2. customto give a precipitate, which
  3. filtrationwas filtered off
  4. dissolutionThe product was redissolved in acetone
  5. additionwater was again added
  6. filtrationThe precipitate was filtered off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-810a03eb1f6a4191be3e963ad3a83fdd
Source dataset
uspto-grants-1984_05
Patent number
US04447425

Reaction notes

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