Ammonia → HCID 68143729, compound

HRID 1415067Notes

Reaction equation

HRID 1415067 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH:13]=[CH:14][C:15]([O:20]C)=[CH:16][C:17]=4[CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[O:22][CH2:23][CH2:24][CH3:25])[CH3:2].COCC(O)C.N.[Li].[Cl-].[NH4+]>O.COCCOC>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[O:22][CH2:23][CH2:24][CH3:25])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 79001-Methoxy-2-propanolHCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 68144810HCID 68144810, compound

Product 1

HCID 68143729HCID 68143729, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Treat a suspension of 1.5 g. of dl-13-ethyl-3-methoxy-17β-propoxygona-1,3,5(10)-triene, 75 ml. of 1,2-dimethoxyethane, 75 ml. of 1-methoxy-2-propanol, and 300 ml. of liquid ammonia with 5.0 g. of lithium. When the reaction ends add 1.5 g. of ammonium chloride and water. Collect the precipitate of dl-13-ethyl-3-methoxy-17β-propoxygona-2,5(10)-diene, and add it to a solution of 50 ml. of methanol, 5 ml. of conc. hydrochloric acid, and 4 ml. of water. Stir for 0.5 hours. Filter off a small amount of insoluble material. Add water to clean solution and extract with ether. Recrystallize from etherpetroleum ether to obtain the title product, m.p. 88°-89°; ultraviolet peak at 242 mμ (ε16,600); infrared peaks at 6.00, 6.19μ.

Workup

  1. additionTreat
  2. additiona suspension of 1.5 g
  3. additionWhen the reaction ends add 1.5 g
  4. customCollect the precipitate of dl-13-ethyl-3-methoxy-17β-propoxygona-2,5(10)-diene
  5. additionadd it to a solution of 50 ml
  6. filtrationFilter off a small amount of insoluble material
  7. extractionAdd water to clean solution and extract with ether
  8. customRecrystallize from etherpetroleum ether

Sources & evidence

ORD record
ord-ce998610952f4587a4f945baff9e5bfb
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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