Dimethylacetamide → 17alpha-Ethynyl-3-methoxyestra-1,3,5(10),8-tetraen-17-ol

HRID 1415058Notes

Reaction equation

HRID 1415058 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C:17]3[CH2:16][CH2:15][C@@:13]4([CH3:14])[C@@H:9]([CH2:10][CH2:11][C:12]4=[O:21])[C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=1.[CH3:22][C:23](N(C)C)=O>>[C:22]([C@:12]1([OH:21])[CH2:11][CH2:10][C@H:9]2[C:8]3[CH2:7][CH2:6][C:5]4[CH:4]=[C:3]([O:2][CH3:1])[CH:20]=[CH:19][C:18]=4[C:17]=3[CH2:16][CH2:15][C@:13]12[CH3:14])#[CH:23]

Participants

3

Reactant 2

HCID 31374DimethylacetamideHCID 11055125Estra-1,3,5(10),8-tetraen-17-one, 3-methoxy-

Product 1

HCID 8673349117alpha-Ethynyl-3-methoxyestra-1,3,5(10),8-tetraen-17-ol

Procedure

Add solid lithium acetylide-ethylenediamine complex (9.5 g) to 3-methoxyestra-1,3,5(10),8-tetraen-17-one (10 g) in dimethylacetamide (100 ml), stir the mixture for 15 hours and then pour into ice water. Extract with ether-benzene (1:1), and wash, dry and evaporate the organic extract. Recrystallize the residue from methanol to obtain dl-17α-ethynyl-3-methoxyestra-1,3,5(10),8-tetraen-17-ol (2.8 g), m.p. 133°-137°; infrared absorption peaks at 3.1 μ, 6.25 μ.

Workup

  1. extractionExtract with ether-benzene (1:1)
  2. washwash
  3. customdry
  4. customevaporate the organic extract
  5. customRecrystallize the residue from methanol

Sources & evidence

ORD record
ord-ee40eef56911402ba02f096ba1e3efa1
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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