HCID 13537257, compound → HCID 13537261, compound

HRID 986409Notes

Reaction equation

HRID 986409 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[CH2:14]([O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2([CH2:26][CH:27]([OH:42])[CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([O:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH:30]=3)[CH2:25][CH2:24]2)=[CH:19][CH:18]=1)[CH3:15]>CC(C)=O.O>[CH2:14]([O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2([CH2:26][C:27](=[O:42])[CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([O:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH:30]=3)[CH2:24][CH2:25]2)=[CH:19][CH:18]=1)[CH3:15]

Participants

5

Reactant 2

HCID 13537257HCID 13537257, compoundHCID 131709961Jones' reagent

Product 1

HCID 13537261HCID 13537261, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Jones reagent (2 ml, prepared by the method described in Fieser and Fieser Vol. 1, p. 142) is added dropwise to a stirring solution of 1-(4-ethoxyphenyl)-1-(3-(3-phenoxyphenyl)-2-hydroxypropyl)-cyclopropane (0.25 g) in acetone (5 ml) whilst maintaining the temperature below 5° C. After 15 min. the mixture is allowed to warm up to room temperature over 4 h, diluted with water, extracted with diethyl ether (x3), washed with water, dried and the solvent evaporated under reduced pressure. The product is purified by thin layer chromatography on silica gel diluted with 15% diethyl ether in petroleum ether (b.p. 60°-80° C.). Yield 0.03 g, nD 1.5580.

Workup

  1. temperaturewhilst maintaining the temperature below 5° C
  2. extractionextracted with diethyl ether (x3)
  3. washwashed with water
  4. customdried
  5. customthe solvent evaporated under reduced pressure
  6. customThe product is purified by thin layer chromatography on silica gel
  7. additiondiluted with 15% diethyl ether in petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-e374fe9ae6904b938838646ffa978312
Source dataset
uspto-grants-1987_12
Patent number
US04713392

Reaction notes

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