Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 3-(4-benzyloxy-3-cyclopentyl-phenyl)prop-2-enoate

HRID 1465115Notes

Reaction equation

HRID 1465115 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])C=CC=CC=1>ClCCl>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[CH:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:11][C:10]=1[CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 593950074-Benzyloxy-3-cyclopentyl-benzaldehyde

Product 1

HCID 67455985Ethyl 3-(4-benzyloxy-3-cyclopentyl-phenyl)prop-2-enoateYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-benzyloxy-3-cyclopentyl-benzaldehyde (1.3 g, 4.64 mmol) and ethyl 2-triphenylphosphoranylideneacetate (1.6 g, 4.64 mmol) in dichloromethane (12 mL) was heated at reflux for 24 h. The reaction was cooled to room temperature and concentrated in vacuo. Purification by silica gel chromatography (0-10% ethyl acetate/hexanes) yielded ethyl 3-(4-benzyloxy-3-cyclopentyl-phenyl)prop-2-enoate (1.2 g, 81% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 7.61-7.57 (m, 2H), 7.52 (dd, J=2.1, 8.5 Hz, 1H), 7.46-7.39 (m, 4H), 7.33 (t, J=7.1 Hz, 1H), 7.06 (d, J=8.5 Hz, 1H), 6.49 (d, J=16 Hz, 1H), 5.18 (s, 2H), 4.16 (q, J=7.1 Hz, 2H), 3.32-3.27 (m, 1H), 1.99-1.92 (m, 2H), 1.74-1.67 (m, 2H), 1.65-1.58 (m, 4H), 1.24 (t, J=7 Hz, 3 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 h
  3. concentrationconcentrated in vacuo
  4. customPurification by silica gel chromatography (0-10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-dfc6c602f0264b359c1797d3866f1194
Source dataset
uspto-grants-2015_04
Patent number
US08999976B2

Reaction notes

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