Ammonia → HCID 54173305, compound

HRID 1578684Notes

Reaction equation

HRID 1578684 reaction equation
N.[CH3:2][O:3][C:4]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:9]([C@H:10]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:13]3([CH2:17][CH:16]([OH:18])[CH2:15][O:14]3)[CH2:12][CH2:11]4)[CH2:8][CH2:7][C:6]=2[CH:5]=1.O1CCCC1.[Li]>CO.CC(C)(O)C>[CH3:2][O:3][C:4]1[CH2:5][C:6]2[CH2:7][CH2:8][C@@H:9]3[C@@H:23]([C:24]=2[CH2:25][CH:26]=1)[CH2:22][CH2:21][C@@:19]1([CH3:20])[C@H:10]3[CH2:11][CH2:12][C:13]21[CH2:17][CH:16]([OH:18])[CH2:15][O:14]2

Participants

7

Reactant 4

HCID 222Ammonia2×HCID 8028TetrahydrofuranHCID 3028194LithiumHCID 22788009HCID 22788009, compound

Product 1

HCID 54173305HCID 54173305, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6386tert-ButanolSolvent

Procedure

To 122 parts of liquid ammonia under reflux is added, with vigorous agitation, a solution of 3 parts of 4',5'-dihydro-3-methoxyspiro[estra-1,3,5(10)-triene 17,2'(3'H)-furan]-4'-ol in a mixture of 81 parts of tetrahydrofuran and 72 parts of 1,1-dimethylethanol, followed -- portionwise -- by 2 parts of lithium wire cut into small pieces. Approximately 2 hours later, 5 parts of methanol is slowly introduced. After an additional 45 minutes, the blue color originally characteristic of the reaction mixture has disappeared, at which point the ammonia is allowed to evaporate and 500 parts of water is added to the residue. The precipitate which forms is filtered off, washed with water, dried in air, and recrystallized from ethyl acetate to give 4',5'-dihydro-3-methoxyspiro[estra-2,5(10)-diene-17,2'(3'H)-furan]-4'-ol melting at 152°-155°.

Workup

  1. additionis added, with vigorous agitation
  2. customto evaporate
  3. addition500 parts of water is added to the residue
  4. filtrationThe precipitate which forms is filtered off
  5. washwashed with water
  6. customdried in air
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6712205cf7124e1bbc570ef2bd6740c2
Source dataset
uspto-grants-1976_02
Patent number
US03939155

Reaction notes

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