Hydrochloric Acid → Gon-4-en-3-one, 13-ethyl-17-hydroxy-, (17beta)-(+-)-

HRID 1077180

Reaction equation

HRID 1077180 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH2:13][CH:14]=[C:15]([O:20]C)[CH2:16][C:17]=4[CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:22])[CH3:2].Cl.O.CCOCC>CO>[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[OH:22])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 101950(17Beta)-13-Ethyl-3-methoxygona-2,5(10)-dien-17-ol

Product 1

HCID 10039774Gon-4-en-3-one, 13-ethyl-17-hydroxy-, (17beta)-(+-)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 13β-ethyl-3-methoxy-gona-2,5(10)-dien-17β-ol (0.47 g.) in hot methanol (25 cc.). Add 3N hydrochloric acid (15 cc.) and keep the mixture at 70° C. under nitrogen for 1 hour. Add water and work up with ether and chromatograph the resulting gum on activated alumina (40 g.). Elute with ether to give a fraction (0.2 g.) which on recrystallization from light petroleum gives 13β-ethyl-17β-hydroxy-gon-4-en-3-one; m.p. 153°-5° C; ultra-violet absorption peak at 240 mμ (ε 16,300).

Workup

  1. customat 70° C.
  2. customfor 1 hour
  3. washElute with ether
  4. customto give a fraction (0.2 g.) which
  5. customon recrystallization from light petroleum

Sources & evidence

ORD record
ord-1a5af62c81a946a696728be7a323e44c
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Linked notes

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