1-Methylpyrrole → 1-(2,4-Dimethyl-5-thiazolyl)-1-(1-methyl-2-pyrrolyl)ethanol

HRID 2831

Reaction equation

HRID 2831 reaction equation
C([Li])CCC.CN(CCN(C)C)C.[CH3:14][N:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1.[C:20]([C:23]1[S:27][C:26]([CH3:28])=[N:25][C:24]=1[CH3:29])(=[O:22])[CH3:21]>C(OCC)C>[CH3:28][C:26]1[S:27][C:23]([C:20]([C:16]2[N:15]([CH3:14])[CH:19]=[CH:18][CH:17]=2)([OH:22])[CH3:21])=[C:24]([CH3:29])[N:25]=1

Participants

6

Reactant 4

HCID 73041-MethylpyrroleHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 5208882,4-Dimethyl-5-acetylthiazoleHCID 178418339Butyllithium

Product 1

HCID 189363311-(2,4-Dimethyl-5-thiazolyl)-1-(1-methyl-2-pyrrolyl)ethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

n-Butyllithium (2.5M solution in hexanes, 20 ml) in dry diethyl ether was cooled to -70° C. under dry nitrogen and TMEDA (5.8 g) was added. After 5 minutes, 1-methylpyrrole (5.4 g) in diethyl ether was added dropwise. After a further 15 minutes, 5-acetyl-2,4-dimethylthiazole (4.5 ml) was added dropwise. After 30 minutes the mixture was allowed to warm to room temperature and was then worked up in the usual fashion.

Workup

  1. waitAfter a further 15 minutes
  2. waitAfter 30 minutes the mixture was allowed

Sources & evidence

ORD record
ord-a84f7dd10911495d860973d4009ad6f3
Source dataset
uspto-grants-1998_03
Patent number
US05731335

Linked notes

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