HCID 54522360, compound → HCID 19611380, compound

HRID 1602497Notes

Reaction equation

HRID 1602497 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([CH:10]=[CH:11][C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=[O:16])[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>O1CCCC1.[C].[Pd]>[C:1]([C:5]1[N:6]=[C:7]([CH2:10][CH2:11][C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=[O:16])[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 54522360HCID 54522360, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19611380HCID 19611380, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-[2-(4-tert-Butyl-2-thiazolyl)vinyl]benzoic acid (1.20 g, 4.18 mmol) was dissolved in tetrahydrofuran (24 ml), 10% palladium-carbon powder (0.2 g) was added to the solution, and the mixture was stirred at room temperature for 3 hours in an atmosphere of hydrogen. The reaction solution was filtered and the resulting filtrate was concentrated under reduced pressure. By crystallizing the resulting residue from diethyl ether-hexane, 3-[2-(4-tert-butyl-thiazolyl)ethyl]benzoic acid (1.12 g, 93%) was obtained.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe resulting filtrate was concentrated under reduced pressure
  3. customBy crystallizing the resulting residue from diethyl ether-hexane

Sources & evidence

ORD record
ord-1bad671aaf194e74bee82da5adbd8534
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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