Epichlorohydrin → HCID 57508919, compound

HRID 2240822Notes

Reaction equation

HRID 2240822 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([C:8](=[O:20])[CH2:9][CH2:10][C:11]2[CH:16]=[C:15]([CH3:17])[C:14]([OH:18])=[C:13]([CH3:19])[CH:12]=2)=[C:5]2[CH2:21][CH2:22][C:23]([CH3:26])([CH3:25])[CH2:24][C:4]=12)[CH3:2].[CH2:27]([CH:29]1[O:31][CH2:30]1)Cl>C(O)(C)C.[OH-].[Na+].C(#N)C>[CH3:19][C:13]1[CH:12]=[C:11]([CH2:10][CH2:9][C:8]([C:6]2[S:7][C:3]([CH2:1][CH3:2])=[C:4]3[CH2:24][C:23]([CH3:25])([CH3:26])[CH2:22][CH2:21][C:5]=23)=[O:20])[CH:16]=[C:15]([CH3:17])[C:14]=1[O:18][CH2:27][CH:29]1[CH2:30][O:31]1

Participants

6

Reactant 2

HCID 7835EpichlorohydrinHCID 11852433HCID 11852433, compound

Product 1

HCID 57508919HCID 57508919, compoundYield 58.6%

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 6342AcetonitrileSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-(4-hydroxy-3,5-dimethyl-phenyl)-propan-1-one (75 mg, 0.20 mmol) in isopropanol (4 mL) and 3 N aq. NaOH (1.7 mL) is treated with epichlorohydrine (75 mg, 0.60 mmol) and the mixture is stirred at rt for 1 h. The mixture is diluted with acetonitrile (1 mL) and separated by prep. HPLC (Phenomenex Aqua, 75×30 mm ID, 10 μm, 10-95% acetonitrile in water containing 0.5% formic acid) to give 3-(3,5-dimethyl-4-oxiranylmethoxy-phenyl)-1-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propan-1-one (50 mg) as a colourless resin; LC-MS: tR=1.21 min, [M+1]=427.41.

Workup

  1. customseparated by prep

Sources & evidence

ORD record
ord-83056928ed7a40f39bf318373d469796
Source dataset
uspto-grants-2010_05
Patent number
US07723378B2

Reaction notes

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