(E)-ethyl 3-(4-(benzyloxy)-3,5-difluorophenyl)-2-methylacrylate → HCID 59419852, compound

HRID 2167397Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10]([F:24])=[C:11](/[CH:16]=[C:17](\[CH3:23])/[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:12]=[CH:13][C:14]=1[F:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:32][C:33]1[C:38]([F:39])=[CH:37][C:36](/[CH:40]=[C:41](\[CH3:47])/[C:42]([O:44][CH2:45][CH3:46])=[O:43])=[CH:35][C:34]=1[F:48])C1C=CC=CC=1>CCOC(C)=O.[C].[Pd]>[F:39][C:38]1[CH:37]=[C:36]([CH2:40][CH:41]([CH3:47])[C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH:35]=[C:34]([F:48])[C:33]=1[OH:32].[CH2:1]([O:8][C:9]1[C:10]([F:24])=[C:11]([CH2:16][CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:12]=[CH:13][C:14]=1[F:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Into a 100-mL round-bottom flask, was placed a solution of ethyl (2E)-3-[3-(benzyloxy)-2,4-difluorophenyl]-2-methylprop-2-enoate and ethyl (2E)-3-[4-(benzyloxy)-3,5-difluorophenyl]-2-methylprop-2-enoate (4 g, 12.04 mmol, 1.00 equiv) in EtOAc (50 ml) and palladium carbon (2.5 g). Into the resulting mixture was then introduced H2(g). The resulting solution was stirred overnight at 25° C. The solids were filtered out and the resulting mixture was concentrated under vacuum. The resulting residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:4) to yield ethyl 3-(3,5-difluoro-4-hydroxyphenyl)-2-methylpropanoate and ethyl 3-(3-(benzyloxy)-2,4-difluorophenyl)-2-methylpropanoate as colorless oil.

Workup

customInto a 100-mL round-bottom flask, was placed
filtrationThe solids were filtered out
concentrationthe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record: ord-18c1680e8cc94f5898d2035f3703607f
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045454B2

Reaction notes

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