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Methyl 3-[4-[3-[4-hexyl-2-(4-methylphenyl)thiazol-5-yl]propenoyl]-2-methylphenyl]acrylate → Methyl 3-[4-[3-[4-hexyl-2-(4-methylphenyl)thiazol-5-yl]propionyl]-2-methylphenyl]propionate

HRID 1951604
Notes
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Reaction equation

HRID 1951604 reaction equation
[CH2:1]([C:7]1[N:8]=[C:9]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)[S:10][C:11]=1[CH:12]=[CH:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[CH:23][C:24]([O:26][CH3:27])=[O:25])=[C:18]([CH3:28])[CH:17]=1)=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H][H]>CO.O1CCCC1.[C].[Pd]>[CH2:1]([C:7]1[N:8]=[C:9]([C:29]2[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=2)[S:10][C:11]=1[CH2:12][CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[C:18]([CH3:28])[CH:17]=1)=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 69000546Methyl 3-[4-[3-[4-hexyl-2-(4-methylphenyl)thiazol-5-yl]propenoyl]-2-methylphenyl]acrylateHCID 178418361HCID 178418361, compound

Product 1

HCID 16755796Methyl 3-[4-[3-[4-hexyl-2-(4-methylphenyl)thiazol-5-yl]propionyl]-2-methylphenyl]propionateYield 41%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalyst
HCID 887
Methanol
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

The obtained methyl 3-[4-[3-[4-hexyl-2-(4-methylphenyl)thiazol-5-yl]propenoyl]-2-methylphenyl]acrylate (112 mg, 0.230 mmol) was dissolved in methanol (1 mL) and tetrahydrofuran (1 mL). 10% palladium carbon (22 mg) was added to the solution to cause replacement of hydrogen in the system. The mixture was stirred at room temperature for 3 hours. The reaction mixture was filtrated with Celite. The filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography with hexane/ethyl acetate (5:1, v/v) to give the desired compound (46 mg) as colorless oil (yield 41%).

Workup

  1. filtrationThe reaction mixture was filtrated with Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography with hexane/ethyl acetate (5:1

Sources & evidence

ORD record
ord-376b303d314049f3a45ad3960a727656
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08404726B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes