Ammonia → HCID 68144537, compound

HRID 1414992Notes

Reaction equation

HRID 1414992 reaction equation
N.[CH:2]([C@:5]12[CH2:13][CH2:12][C@@H:11]3[C:14]4[CH:15]=[CH:16][C:17]([O:22][CH3:23])=[CH:18][C:19]=4[CH2:20][CH2:21][C@H:10]3[C@@H:9]1[CH2:8][CH2:7][C@@H:6]2[OH:24])([CH3:4])[CH3:3].[Li].C(O)C>O1CCCC1.O>[CH:2]([C@:5]12[CH2:13][CH2:12][C@@H:11]3[C:14]4[CH2:15][CH:16]=[C:17]([O:22][CH3:23])[CH2:18][C:19]=4[CH2:20][CH2:21][C@H:10]3[C@@H:9]1[CH2:8][CH2:7][C@@H:6]2[OH:24])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 3028194LithiumHCID 68143773HCID 68143773, compound

Product 1

HCID 68144537HCID 68144537, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add liquid ammonia (100 cc.) to 13β-isopropyl-3-methoxy-gona-1,3,5(10)-trien-17β-ol (0.5 g.) in tetrahydrofuran (50 cc.) followed by lithium metal (0.5 g.), and stir the solution for 10 minutes. Then add ethanol (6 cc.) dropwise. When the blue color is discharged, add water and extract the product with ether. Evaporate the washed and dried extracts to give crude 13β-isopropyl -3-methoxy-gona-2,5(10)-dien-17β-ol (0.5 g.) as colorless gum.

Workup

  1. extractionextract the product with ether
  2. customEvaporate the
  3. washwashed
  4. customdried extracts

Sources & evidence

ORD record
ord-261bb8ced79e4ee2850997d166c0f48f
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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