Water → 4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(1-tert-butylcarbonylimidazol-2-ylethynyl)cyclohexan-1-one

HRID 343564Notes

Reaction equation

HRID 343564 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:22]#[CH:23])[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:24]([C:28]([N:30]1[CH:34]=[CH:33][N:32]=[C:31]1I)=[O:29])([CH3:27])([CH3:26])[CH3:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C(N(CC)CC)C.[Cu]I>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:22]#[C:23][C:31]4[N:30]([C:28]([C:24]([CH3:27])([CH3:26])[CH3:25])=[O:29])[CH:34]=[CH:33][N:32]=4)[CH2:16][CH2:17][C:18](=[O:21])[CH2:19][CH2:20]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 108289304-(3-Cyclopentyloxy-4-methoxyphenyl)-4-ethynylcyclohexan-1-oneHCID 536436291-Tert.-butylcarbonyl-2-iodoimidazole

Product 1

HCID 572810394-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(1-tert-butylcarbonylimidazol-2-ylethynyl)cyclohexan-1-oneYield 43.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-ethynylcyclohexan-1-one (0.28g, 0.9 mmol) and 1-tert.-butylcarbonyl-2-iodoimidazole (0.29 g, 0.97 mmol) in triethylamine (5 mL) under an argon atmosphere were added tetrakis(triphenyl-phosphine)palladium(0) (0.042 g, 4%), copper(I) iodide (0.005 g, 6%), and a small crystal of triphenylphosphine, and the mixture was heated at 80°-85° C. for 1 h. Water was added and the mixture was extracted three times with dichloromethane, was dried (magnesium sulfate) and was evaporated. Purification by flash chromatography, eluting with 3:7 ethyl acetate:hexanes provided 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(1-tert-butylcarbonylimidazol-2-ylethynyl)cyclohexan-1-one (0.18 g, 4%), as a colorless oil. 1H-NMR (400 MHz, CDCl3) δ 7.36 (s, 1H), 7.20 (d, J=2.1 Hz, 1H), 7.17 (dd, J=8.5, 2.1 Hz, 1H), 7.01 (s, 1H), 6.85 (d, J=8.5 Hz, 1H), 4.85 (m, 1H), 3.84 (s, 3H), 3.18 (m, 2H), 2.44 (m, 4H), 2.22 (m, 2H), 1.8-2.0 (m, 6H), 1.6 (m, 11H) ppm.

Workup

  1. extractionthe mixture was extracted three times with dichloromethane
  2. dry with materialwas dried (magnesium sulfate)
  3. customwas evaporated
  4. customPurification by flash chromatography
  5. washeluting with 3:7 ethyl acetate

Sources & evidence

ORD record
ord-00af756076ee4456b7c81d7079054d09
Source dataset
uspto-grants-1999_01
Patent number
US05861421

Reaction notes

Loading…