Cyclopentanol → 1-(Cyclopentyloxy)-4-methoxybenzene

HRID 1243054

Reaction equation

HRID 1243054 reaction equation
CC1C=C2C(N=CC=C2)=C2C=1C=CC=N2.C([O-])([O-])=O.[Cs+].[Cs+].I[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1.[CH:31]1([OH:36])[CH2:35][CH2:34][CH2:33][CH2:32]1>[Cu]I>[CH:31]1([O:36][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 7298CyclopentanolHCID 10796Cesium carbonateHCID 696764-IodoanisoleHCID 727915-Methyl-1,10-phenanthroline

Product 1

HCID 155310071-(Cyclopentyloxy)-4-methoxybenzeneYield 67%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
110 °C

Procedure

A test tube was charged with CuI (20 mg, 0.10 mmol, 10 mol %), 5-methyl-1,10-phenanthroline (39 mg, 0.20 mmol, 20 mol %), Cs2CO3 (652 mg, 2.0 mmol), 4-iodoanisole (234 mg, 1.0 mmol) and cyclopentanol (1.0 mL). The test tube was sealed and the reaction mixture was stirred at 110° C. for 24 h. The resulting suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel eluting with diethyl ether. The filtrate was concentrated. Purification of the residue by flash chromatography on silica gel (2×20 cm; pentane/diethyl ether 30:1) provided 128 mg (67% yield) of the title compound as a colorless oil.

Workup

  1. customThe test tube was sealed
  2. temperatureThe resulting suspension was cooled to room temperature
  3. filtrationfiltered through a 0.5×1 cm pad of silica gel eluting with diethyl ether
  4. concentrationThe filtrate was concentrated
  5. customPurification of the residue by flash chromatography on silica gel (2×20 cm; pentane/diethyl ether 30:1)

Sources & evidence

ORD record
ord-4c514309c5b345e8b19e0ec62cd6758c
Source dataset
uspto-grants-2006_10
Patent number
US07115784B2

Linked notes

Loading…