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

HRID 2167397
Notes
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Reaction equation

HRID 2167397 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 59419841(E)-ethyl 3-(4-(benzyloxy)-3,5-difluorophenyl)-2-methylacrylateHCID 90442472HCID 90442472, compound

Product 2

HCID 59419852HCID 59419852, compoundHCID 90406564HCID 90406564, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent
HCID 178418390
HCID 178418390, compound
Solvent

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

  1. customInto a 100-mL round-bottom flask, was placed
  2. filtrationThe solids were filtered out
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes