Ammonia → 17beta-Ethoxy-13-ethylgon-4-en-3-one

HRID 1415064Notes

Reaction equation

HRID 1415064 reaction equation
[Li].[CH2:2]([O:4][C@@H:5]1[C@:13]2([CH2:14][CH3:15])[C@H:8]([C@@H:9]3[CH2:23][CH2:22][C:21]4[CH:20]=[C:19]([O:24]C)[CH:18]=[CH:17][C:16]=4[C@H:10]3[CH2:11][CH2:12]2)[CH2:7][CH2:6]1)[CH3:3].COCC(O)C.N>COCCOC>[CH2:2]([O:4][C@@H:5]1[C@:13]2([CH2:14][CH3:15])[C@H:8]([C@@H:9]3[CH2:23][CH2:22][C:21]4[C@H:16]([CH2:17][CH2:18][C:19](=[O:24])[CH:20]=4)[C@H:10]3[CH2:11][CH2:12]2)[CH2:7][CH2:6]1)[CH3:3]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 79001-Methoxy-2-propanolHCID 3028194LithiumHCID 6814505317beta-Ethoxy-13-ethyl-3-methoxygona-1,3,5(10)-triene

Product 1

HCID 8673439617beta-Ethoxy-13-ethylgon-4-en-3-one

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Add 2.0 g. of lithium to a suspension of 2.0 g. of dl-17β-ethoxy-13-ethyl-3-methoxygona-1,3,5(10)-triene, 90 ml. of 1,2-dimethoxyethane, 100 ml. of 1-methoxy-2-propanol, and 300 ml. of ammonia while stirring. Treat with 2.0 g. of ammonium chloride and water, filter off the precipitate and add it to 80 ml. of methanol, 4 ml. of water, and 5 ml. of conc. hydrochloric acid. Stir for one hour and dilute with water. Extract the product with ether and recrystallize it successively from methanol-water and petroleum ether-ether to obtain the title substance, m.p. 95°-97°; ultraviolet peak at 244 mμ (15,900); infrared peak at 6.0 μ.

Workup

  1. additionAdd 2.0 g
  2. additionTreat with 2.0 g
  3. filtrationof ammonium chloride and water, filter off the precipitate
  4. additionadd it to 80 ml
  5. additiondilute with water
  6. extractionExtract the product with ether
  7. customrecrystallize it successively from methanol-water and petroleum ether-ether
  8. customto obtain the title substance, m.p. 95°-97°

Sources & evidence

ORD record
ord-9a1c63eed6644c61b2dce3528146fd98
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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