Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 6-methoxy-4-(2-methoxyethyl)-hex-2-enoate

HRID 222561Notes

Reaction equation

HRID 222561 reaction equation
[CH:1]([CH:3]([CH2:8][CH2:9][O:10][CH3:11])[CH2:4][CH2:5][O:6][CH3:7])=O.[C:12]([CH:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:14][CH2:15][CH3:16])=[O:13]>C(Cl)Cl>[CH3:7][O:6][CH2:5][CH2:4][CH:3]([CH2:8][CH2:9][O:10][CH3:11])[CH:1]=[CH:17][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 578598393-Formyl-1,5-dimethoxypentane

Product 1

HCID 76645421Ethyl 6-methoxy-4-(2-methoxyethyl)-hex-2-enoateYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 23 (1.10 g, 6.88 mmol) and (carbethoxymethylene)triphenylphosphorane (2.63 g, 7.56 mmol, 1.1 equiv) was refluxed in CH2Cl2 (8.2 mL) for 24 h. The solvent was removed at reduced pressure. The oily residue was chromatographed [silica, hexanes/diethyl ether (1:1)] to yield a pale yellow oil (1.31 g, 88%): 1H NMR δ 1.50-1.62 (m, 2H), 1.69-1.85 (m, 2H), 2.45-2.51 (m, 1H), 3.23-3.33 (m, 10H), 5.79 (d, J=16.1 Hz, 1H), 6.71 (dd, J=9.5 Hz, J2=16.1 Hz, 1H); 13C NMR δ 14.46, 34.42, 36.40, 58.79, 60.48, 70.42, 122.03, 152.01, 166.73; FAB-MS obsd 231.1596, calcd 231.1598 [(M+H)+, M=C12H22O4].

Workup

  1. customThe solvent was removed at reduced pressure
  2. customThe oily residue was chromatographed [silica, hexanes/diethyl ether (1:1)]

Sources & evidence

ORD record
ord-77d6b66f1cbd4378b6e83a5c058184c2
Source dataset
uspto-grants-2012_06
Patent number
US08207329B2

Reaction notes

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