Lithium → HCID 68144569, compound

HRID 1414986Notes

Reaction equation

HRID 1414986 reaction equation
[CH2:1]([C@:4]12[CH2:12][CH2:11][C:10]3[C:13]4[CH:14]=[CH:15][C:16]([O:21][CH3:22])=[CH:17][C:18]=4[CH2:19][CH2:20][C:9]=3[C@@H:8]1[CH2:7][CH2:6][C@@H:5]2[OH:23])[CH2:2][CH3:3].[Li]>O1CCCC1.NC1C=CC=CC=1.N>[CH2:1]([C@:4]12[CH2:12][CH2:11][C@@H:10]3[C:13]4[CH:14]=[CH:15][C:16]([O:21][CH3:22])=[CH:17][C:18]=4[CH2:19][CH2:20][C@H:9]3[C@@H:8]1[CH2:7][CH2:6][C@@H:5]2[OH:23])[CH2:2][CH3:3]

Participants

6

Reactant 2

HCID 3028194LithiumHCID 68143930HCID 68143930, compound

Product 1

HCID 68144569HCID 68144569, compoundYield 99.4%

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 6115AnilineSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add 13β-n-propyl-3-methoxy-gona-1,3,5(10),8-tetraen-17β-ol (3.1 g.) dissolved in a mixture of tetrahydrofuran (10 cc.) and freshly distilled aniline (60 cc.) to liquid ammonia (160 cc.) and add lithium metal (1.5 g.) in small pieces. Stir the reaction mixture for 3 hours, then quench with solid ammonium chloride (12.5 g.) and take up in water. Ether-extract the product and evaporate the washed and dried extracts to obtain a semisolid residue of crude 13β-n-propyl-3-methoxy-gona-1,3,5(10)-trien-17β-ol (3.1 g.); ultraviolet absorption peak at 279 mμ (ε1,800).

Workup

  1. customquench with solid ammonium chloride (12.5 g.)
  2. extractionEther-extract the product
  3. customevaporate the
  4. washwashed
  5. customdried extracts

Sources & evidence

ORD record
ord-9a7604c6f8d54c25b1a3316dbfd073c1
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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