Epichlorohydrin → 3-(3,5-Dimethyl-4-oxiranylmethoxy-phenyl)-1-(5-ethyl-4-phenyl-thiophen-2-yl)-propan-1-one

HRID 552282Notes

Reaction equation

HRID 552282 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]([CH2:24][CH3:25])=[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[CH3:26].[CH2:27]([CH:29]1[O:31][CH2:30]1)Cl>CC(O)C.[OH-].[Na+].O>[CH3:26][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]([C:13]2[S:14][C:15]([CH2:24][CH3:25])=[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][CH2:27][CH:29]1[CH2:30][O:31]1

Participants

6

Reactant 2

HCID 7835EpichlorohydrinHCID 592489883-(4-Hydroxy-3,5-dimethyl-phenyl)-1-(5-ethyl-4-phenyl-thiophen-2-yl)-propan-1-one

Product 1

HCID 866401723-(3,5-Dimethyl-4-oxiranylmethoxy-phenyl)-1-(5-ethyl-4-phenyl-thiophen-2-yl)-propan-1-oneYield 47%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-(4-hydroxy-3,5-dimethyl-phenyl)-1-(5-ethyl-4-phenyl-thiophen-2-yl)-propan-1-one (296 mg, 0.81 mmol) in 2-propanol (2.5 mL) and 3 N aq. NaOH (1 mL) is treated with epichlorohydrine (150 mg, 1.63 mmol) and the mixture is stirred at it 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 4:1 to give 3-(3,5-dimethyl-4-oxiranylmethoxy-phenyl)-1-(5-ethyl-4-phenyl-thiophen-2-yl)-propan-1-one (160 mg) as a pale yellow oil; LC-MS: tR=1.16 min, [M+1]+=421.22, 1H NMR (CDCl3): δ 7.58 (s, 1H), 7.45-7.30 (m, 5H), 6.88 (m, 2H), 3.99 (dd, J=2.9, 11.1 Hz, 1H), 3.72 (dd, J=5.8, 11.1 Hz, 1H), 3.38-3.31 (m, 1H), 3.19-3.11 (m, 2H), 2.98-2.85 (m, 5H), 2.72-2.67 (m, 1H), 2.26 (s, 6H), 1.30 (t, J=7.6 Hz, 3H).

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 4:1

Sources & evidence

ORD record
ord-fce3ffcc4e134687bba762377f2b503d
Source dataset
uspto-grants-2011_05
Patent number
US07951794B2

Reaction notes

Loading…