Epichlorohydrin → HCID 86640169, compound

HRID 552273Notes

Reaction equation

HRID 552273 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH2:9][CH2:10][C:11]([C:13]2[S:14][C:15]([CH3:24])=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:17]=2)=[O:12])=[CH:4][C:3]=1[CH3:25].[CH2:26]([CH:28]1[O:30][CH2:29]1)Cl>CC(O)C.[OH-].[Na+].O>[CH3:25][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]([C:13]2[S:14][C:15]([CH3:24])=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:17]=2)=[O:12])[CH:6]=[C:7]([CH3:8])[C:2]=1[O:1][CH2:26][CH:28]1[CH2:29][O:30]1

Participants

6

Reactant 2

HCID 7835EpichlorohydrinHCID 59248994HCID 59248994, compound

Product 1

HCID 86640169HCID 86640169, compoundYield 26.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-(4-hydroxy-3,5-dimethyl-phenyl)-1-(5-methyl-4-phenyl-thiophen-2-yl)-propan-1-one (300 mg, 0.86 mmol) in 2-propanol (7.5 mL) and 3 N aq. NaOH (2.5 mL) is treated with epichlorohydrine (158 mg, 1.72 mmol) and the mixture is stirred at rt for 24 h, then diluted with water and extracted with EA. The solvent of the organic extract is evaporated and the residue is purified by CC on silica gel eluting with hepaten:EA 5:1 to give 3-(3,5-dimethyl-4-oxiranylmethoxy-phenyl)-1-(5-methyl-4-phenyl-thiophen-2-yl)-propan-1-one (92 mg) as an oil; LC-MS: tR=1.13 min, [M+1]+=407.24.

Workup

  1. extractionextracted with EA
  2. extractionThe solvent of the organic extract
  3. customis evaporated
  4. customthe residue is purified by CC on silica gel eluting with hepaten:EA 5:1

Sources & evidence

ORD record
ord-65dab2e40f464752ba0b81c28d942119
Source dataset
uspto-grants-2011_05
Patent number
US07951794B2

Reaction notes

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