Potassium Carbonate → 2-Phenoxy-1-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone

HRID 2240832Notes

Reaction equation

HRID 2240832 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].Br[CH2:8][C:9]([C:11]1[S:12][C:13]([CH3:22])=[C:14]2[CH2:19][C:18]([CH3:21])([CH3:20])[CH2:17][CH2:16][C:15]=12)=[O:10]>CC(C)=O>[O:4]([CH2:8][C:9]([C:11]1[S:12][C:13]([CH3:22])=[C:14]2[CH2:19][C:18]([CH3:21])([CH3:20])[CH2:17][CH2:16][C:15]=12)=[O:10])[C:1]1[CH:14]=[CH:15][CH:11]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 575089072-Bromo-1-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone

Product 1

HCID 575089292-Phenoxy-1-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To the appropriate phenols (50 μmol, 2 eq.) and K2CO3 (10.5 mg, 75 μmol) a solution of 2-bromo-1-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone (7.5 mg, 25 μmol) in acetone (0.7 mL) is added. The suspension is stirred at rt for 18 h before it is filtered. The solvent of the filtrate is evaporated and the crude product is purified by prep. HPLC (Symmetry C18 5 μm, 19×50 mm, 20-95% acetonitrile in water containing 0.5% formic acid) to give the desired 2-phenoxy-1-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone.

Workup

  1. filtrationis filtered
  2. customThe solvent of the filtrate is evaporated
  3. customthe crude product is purified by prep

Sources & evidence

ORD record
ord-eda52299fa9f418e8dcad06142d2a4c2
Source dataset
uspto-grants-2010_05
Patent number
US07723378B2

Reaction notes

Loading…