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

HRID 383379Notes

Reaction equation

HRID 383379 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, 3H).

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-bb9d1d368552498dbfaf036d11f0b108
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

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