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

HRID 1415066Notes

Reaction equation

HRID 1415066 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 elute 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
  5. washChromatograph the residue on alumina (Grade I neutral) in hexane and elute the product with ether

Sources & evidence

ORD record
ord-c356065c28b14b05b7d7f21752de551a
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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