Ammonia → HCID 68144451, compound

HRID 1077223Notes

Reaction equation

HRID 1077223 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:20]2[C@H:9]3[CH2:10][CH2:11][C@@:12]4([CH2:18][CH3:19])[C@H:16]([C@@H:8]3[CH2:7][CH:6]([CH3:23])[C:5]=2[CH:4]=1)[CH2:15][CH2:14][C@@H:13]4[OH:17].N.[Li].C(O)C>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH2:4][C:5]2[CH:6]([CH3:23])[CH2:7][C@H:8]3[C@H:16]4[C@@:12]([CH2:18][CH3:19])([C@@H:13]([OH:17])[CH2:14][CH2:15]4)[CH2:11][CH2:10][C@@H:9]3[C:20]=2[CH2:21][CH:22]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 3028194LithiumHCID 6814444413-Ethyl-3-methoxy-6-methylgona-1,3,5(10)-trien-17beta-ol

Product 1

HCID 68144451HCID 68144451, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Add dl-3-methoxy-17β-hydroxy-6-methyl-13-ethylgona-1,3,5(10)-triene (6.80 g) in tetrahydrofuran (200 cc) to liquid ammonia (800 cc) containing tetrahydrofuran (250 cc). Add lithium metal (3.5 g) portionwise and stir the solution for 1.75 hours. Discharge the blue color by dropwise addition of absolute ethanol over 0.25 hours followed by water (2,000 cc). Filter, wash and dry to obtain the dl-3-methoxy-17β-hydroxy-6-methyl-13-ethylgona-2,5(10)-diene (6.5 g), m.p. 176°-182°, λ max. KBr 3.05 μ, 5.90 μ, 6.0 μ, no absorption in the ultraviolet above 220 mμ.

Workup

  1. filtrationFilter
  2. washwash
  3. customdry

Sources & evidence

ORD record
ord-d2a27d0e303741e1a7656252ff9c05a1
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

Loading…