Epichlorohydrin → HCID 57508917, compound

HRID 2240821Notes

Reaction equation

HRID 2240821 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]3[CH2:21][C:20]([CH3:23])([CH3:22])[CH2:19][CH2:18][C:17]=23)=[O:12])=[CH:4][C:3]=1[CH3:25].[CH2:26]([CH:28]1[O:30][CH2:29]1)Cl>C(O)(C)C.[OH-].[Na+].C(OCC)C>[CH3:8][C:7]1[CH:6]=[C:5]([CH2:9][CH2:10][C:11]([C:13]2[S:14][C:15]([CH3:24])=[C:16]3[CH2:21][C:20]([CH3:22])([CH3:23])[CH2:19][CH2:18][C:17]=23)=[O:12])[CH:4]=[C:3]([CH3:25])[C:2]=1[O:1][CH2:26][CH:28]1[CH2:29][O:30]1

Participants

6

Reactant 2

HCID 7835EpichlorohydrinHCID 11852048HCID 11852048, compound

Product 1

HCID 57508917HCID 57508917, compoundYield 58.3%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-(4-hydroxy-3,5-dimethyl-phenyl)-1-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propan-1-one (200 mg, 0.561 mmol) in isopropanol (5 mL) and 3 N aq. NaOH (2 mL) is treated with epichlorohydrine (210 mg, 1.68 mmol) and the mixture is stirred at rt for 6 h before it is diluted with diethyl ether, washed with sat. aq. NaHCO3 solution followed by water, dried over MgSO4 and evaporated. The crude product is purified on prep. TLC plates with heptane:EA 1:1 to give 3-(3,5-dimethyl-4-oxiranylmethoxy-phenyl)-1-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propan-1-one (135 mg) as a yellow oil; LC-MS: tR=1.19 min, [M+1]=413.26.

Workup

  1. washwashed with sat. aq. NaHCO3 solution
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe crude product is purified on prep

Sources & evidence

ORD record
ord-be7639320dae40b1abe4bb50a9aa4154
Source dataset
uspto-grants-2010_05
Patent number
US07723378B2

Reaction notes

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