Ethyl 2-(triphenylphosphoranylidene)propionate → (E)-ethyl 3-(4-(benzyloxy)-3,5-difluorophenyl)-2-methylacrylate

HRID 2167396Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:16]([F:17])=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([O:26][C:27]1[C:28]([F:36])=[C:29]([CH:32]=[CH:33][C:34]=1[F:35])[CH:30]=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[C:44]([CH3:50])[C:45]([O:47][CH2:48][CH3:49])=[O:46])C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:16]([F:17])=[CH:15][C:12](/[CH:13]=[C:44](\[CH3:50])/[C:45]([O:47][CH2:48][CH3:49])=[O:46])=[CH:11][C:10]=1[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([O:26][C:27]1[C:28]([F:36])=[C:29](/[CH:30]=[C:44](\[CH3:50])/[C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH:32]=[CH:33][C:34]=1[F:35])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Into a 100-mL round-bottom flask, was placed 4-(benzyloxy)-3,5-difluorobenzaldehyde and 3-(benzyloxy)-2,4-difluorobenzaldehyde (4 g, 16.11 mmol, 1.00 equiv, crude), ethyl 2-(triphenylphosphoranylidene)propanoate (8.75 g, 24.14 mmol, 1.50 equiv) and toluene (60 mL). The resulting solution was stirred for 12 h at 110° C. The resulting mixture was then concentrated under vacuum. The resulting residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:8) to yield ethyl (2E)-3-[4-(benzyloxy)-3,5-difluorophenyl]-2-methylprop-2-enoate and ethyl (2E)-3-[3-(benzyloxy)-2,4-difluorophenyl]-2-methylprop-2-enoate as yellow oil.

Workup

customInto a 100-mL round-bottom flask, was placed
concentrationThe resulting mixture was then concentrated under vacuum

Sources & evidence

ORD record: ord-e507a5c0b4f04a3d8047bdb2af9d2268
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045454B2

Reaction notes

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