Iodoethane → 17beta-Ethoxy-13-ethyl-3-methoxygona-1,3,5(10)-triene

HRID 1415063Notes

Reaction equation

HRID 1415063 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](I)[CH3:26]>C1(C)C(C)=CC=CC=1>[CH2:25]([O:22][C@@H: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)[CH3:26]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 66432(17beta)-13-Ethyl-3-methoxygona-1,3,5(10)-trien-17-ol

Product 1

HCID 6814505317beta-Ethoxy-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)-trien-17β-ol and 3.83 g. of sodium hydride (50% in oil) for 1.5 hours in xylene (100 ml). Add 14.5 ml. of ethyl iodide and reflux for 22 hours. Acidify with 2N hydrochloric acid and extract the material with benzene. Chromatograph the residue on alumina (Grade I neutral). Elute the product with benzene-ether (1:1). Recrystallize the product from 60 ml. of methanol to obtain dl-17β-ethoxy-13-ethyl-3-methoxygona-1,3,5(10)-triene (2.3 g); m.p. 74°-77°C.

Workup

  1. temperatureReflux
  2. additiona suspension of 5.0 g
  3. additionAdd 14.5 ml
  4. extractionAcidify with 2N hydrochloric acid and extract the material with benzene
  5. washElute the product with benzene-ether (1:1)
  6. customRecrystallize the product from 60 ml

Sources & evidence

ORD record
ord-7b5a22d2bd3f4b309d983bb243ab4fb8
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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