Lithium Hydroxide → HCID 14801346, compound

HRID 2073811Notes

Reaction equation

HRID 2073811 reaction equation
[OH-].[Li+].C([O:11][C@H:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C@H:30]([CH2:31][CH2:32][C@:13]12[CH3:14])[C@:26]1([CH:27]([F:29])[F:28])[C:21]([CH2:22][C:23]2([O:36][CH2:35][CH2:34][O:33]2)[CH2:24][CH2:25]1)=[CH:20][CH2:19]3)(=O)C1C=CC=CC=1>O1CCCC1.CO>[CH2:35]1[CH2:34][O:33][C:23]2([CH2:24][CH2:25][C@@:26]3([CH:27]([F:29])[F:28])[C:21](=[CH:20][CH2:19][C@@H:18]4[C@@H:30]3[CH2:31][CH2:32][C@@:13]3([CH3:14])[C@H:15]4[CH2:16][CH2:17][C@@H:12]3[OH:11])[CH2:22]2)[O:36]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 14801344HCID 14801344, compound

Product 1

HCID 14801346HCID 14801346, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of this 3,3-ethylenedioxy ester (4.73 g) in 50 ml of tetrahydrofuran is chilled to 0° C., treated with 10 ml of 1N lithium hydroxide in methanol and allowed to warm to room temperature. The reaction is monitored by thin layer chromatography. When all of the ester has been hydrolyzed, the solution is concentrated and diluted with ether. The mixture is washed three times with water and once with brine, dried over magnesium sulfate, and concentrated. The residue is crystallized from ethyl acetate/hexane to yield 3,3-ethylenedioxy-19,19-difluoroandrost-5-en-17β-ol as white crystals.

Workup

  1. concentrationthe solution is concentrated
  2. additiondiluted with ether
  3. washThe mixture is washed three times with water
  4. dry with materialonce with brine, dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-70024d273dc1452db027df21d02fb703
Source dataset
uspto-grants-1990_04
Patent number
US04920114

Reaction notes

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