Hydrochloric Acid → 17beta-Allyloxy-13-ethyl-3-methoxygona-1,3,5(10)-triene

HRID 1077245

Reaction equation

HRID 1077245 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][CH3:21])=[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[OH:22])[CH3:2].[H-].[Na+].[CH2:25](Br)[CH:26]=[CH2:27].Cl>C1(C)C(C)=CC=CC=1>[C:26]([O:22][CH:4]1[C@:3]2([CH2:1][CH3:2])[C@H:7]([C@@H:8]3[CH2:19][CH2:18][C:17]4[CH:16]=[C:15]([O:20][CH3:21])[CH:14]=[CH:13][C:12]=4[C@H:9]3[CH2:10][CH2:11]2)[CH2:6][CH2:5]1)(=[CH2:25])[CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 66432(17beta)-13-Ethyl-3-methoxygona-1,3,5(10)-trien-17-ol

Product 1

HCID 8673349217beta-Allyloxy-13-ethyl-3-methoxygona-1,3,5(10)-triene

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Reflux a suspension of 5.0 g. of dl-13-ethyl-3-methoxygona-1,3,5(10)-triene-17β-ol, 100 mg. of xylene, and 3.9 g. of sodium hydride (50% in mineral oil) for 1.5 hours. Add 14.5 ml. of allyl bromide and reflux for 22 hours. Make the reaction mixture acidic with dilute hydrochloric acid and extract the organic layer with sodium bicarbonate solution. Chromatograph the residue on alumina (Grade I neutral) in hexane and eluate the product with ether to obtain dl-17β-allyloxy-13-ethyl-3-methoxygona-1,3,5(10)-triene.

Workup

  1. temperatureReflux
  2. additiona suspension of 5.0 g
  3. additionAdd 14.5 ml
  4. extractionextract the organic layer with sodium bicarbonate solution

Sources & evidence

ORD record
ord-db1a331c08994f5382dc45e5bb1d0a9b
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Linked notes

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