2-Acetylbenzofuran → 1-(2-Benzofuranyl)-1-(4-methyl-5-thiazolyl)ethanol

HRID 2828

Reaction equation

HRID 2828 reaction equation
C([Li])CCC.[CH3:6][C:7]1[N:8]=[C:9]([Si](C)(C)C)[S:10][CH:11]=1.[C:16]([C:19]1[O:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[CH:23]=1)(=[O:18])[CH3:17]>C(OCC)C>[O:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[CH:23]=[C:19]1[C:16]([C:11]1[S:10][CH:9]=[N:8][C:7]=1[CH3:6])([OH:18])[CH3:17]

Participants

5

Reactant 3

HCID 154352-AcetylbenzofuranHCID 116583544-Methyl-2-trimethylsilylthiazoleHCID 178418339Butyllithium

Product 1

HCID 189363601-(2-Benzofuranyl)-1-(4-methyl-5-thiazolyl)ethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

n-Butyllithium (2.5M solution in hexane, 1 equivalent) was added dropwise to a solution of 4-methyl-2-trimethylsilylthiazole (1 equivalent) in dry diethyl ether at -70° C. under an atmosphere of dry nitrogen. After 30 minutes, 2-acetylbenzofuran (1 equivalent) in diethyl ether was added. After 1 hour the mixture was allowed to warm to room temperature and was then quenched by the addition of saturated aqueous sodium hydrogen carbonate. Work up in the normal fashion and column chromatography on silica gel then afforded the title compound.

Workup

  1. waitAfter 1 hour the mixture was allowed
  2. customwas then quenched by the addition of saturated aqueous sodium hydrogen carbonate

Sources & evidence

ORD record
ord-9c11173c9d7a4647bd65210ad622b55b
Source dataset
uspto-grants-1998_03
Patent number
US05731335

Linked notes

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