Acetonitrile → 4-Methyl-1-(4-methyl-thiazol-5-yl)-pent-1-en-3-one

HRID 23442Notes

Reaction equation

HRID 23442 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[CH:7]=O.[Br-].[CH3:10][CH:11]([CH3:34])[C:12](=[O:33])[CH2:13][As+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[CH3:10][CH:11]([CH3:34])[C:12](=[O:33])[CH:13]=[CH:7][C:6]1[S:5][CH:4]=[N:3][C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 5813394-Methylthiazole-5-carboxaldehydeHCID 11465575Arsonium, (3-methyl-2-oxobutyl)triphenyl-, bromide

Product 1

HCID 538148064-Methyl-1-(4-methyl-thiazol-5-yl)-pent-1-en-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared as described in General Method 1 using 1.4 g (11.0 mmol) of 4-methyl-5-thiazolecarbaldehyde (Example A-12), 6.2 g (13.1 mmol) of (3-methyl-2-oxobutyl)triphenylarsonium bromide, 1.8 g (13.1 mmol) of potassium carbonate, 75 mL of acetonitrile, and 0.75 mL of H2O. Chromatography of the residue, eluting with 3:1 hexane:EtOAc gave the title compound.

Workup

  1. customThe title compound was prepared
  2. washChromatography of the residue, eluting with 3:1 hexane

Sources & evidence

ORD record
ord-b6a0b864235042f99a35593d3de787e0
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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