Water → (E)-3-(2,4-dibenzyloxyphenyl)prop-2-enoic acid

HRID 322848

Reaction equation

C([Li])CCC.[CH2:6]([C:8](CC)(P(O)(O)=O)[C:9]([OH:11])=[O:10])C.[CH2:18]([O:25][C:26]1[CH:33]=[C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:31]=[CH:30][C:27]=1C=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>O1CCCC1>[CH2:18]([O:25][C:26]1[CH:33]=[C:32]([O:34][CH2:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:31]=[CH:30][C:27]=1/[CH:6]=[CH:8]/[C:9]([OH:11])=[O:10])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: -70 °C

Procedure

To a solution of 2.5 M n-butyl lithium (3.64 mL) in dry tetrahydrofuran (THF) (20 mL) that is cooled to −70° C. under nitrogen is added a solution of diethyl phosphonoacetic acid (0.89 g) in THF (5 mL). After 30 minutes a solution of 2,4-dibenzyloxybenzaldehyde (1.46 g) in THF (5 mL) is slowly added to the cooled solution so as to maintain the temperature. The resulting mixture is stirred at −70° C. for 3 hours and then at 25° C. for 18 hours. The resulting suspension is treated with water, the THF is removed in vacuo,the residue is extracted with ethyl acetate, the extract is dried and evaporated. The residual solid is recrystallized from isopropanol to yield (E)-3-(2,4-dibenzyloxyphenyl)prop-2-enoic acid as colourless crystals (0.6 g), m.p. 153-155° C. H NMR (DMSO) 5.15 (2H,s), 5.21(2H,s), 6.4(1H,d,J=16 Hz), 6.7(1H,d), 6.85(1H,s), 7.3-7.5(10H,m), 7.6(1H,d), 7.8(1H,d,J=16 Hz).

Workup

temperatureto maintain the temperature
waitat 25° C. for 18 hours
customthe THF is removed in vacuo,the residue
extractionis extracted with ethyl acetate
customthe extract is dried
customevaporated
customThe residual solid is recrystallized from isopropanol

Sources & evidence

ORD record: ord-633593c12a7d4fa1bd1831ffcea2d9aa
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211234B1

Linked notes

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