Ammonium Chloride → Bis(4-methyl-5-thiazolyl)methanol

HRID 1377554Notes

Reaction equation

HRID 1377554 reaction equation
C([Li])CCC.[CH3:6][C:7]1[N:8]=[C:9]([Si](C)(C)C)[S:10][CH:11]=1.[CH3:16][C:17]1[N:18]=[CH:19][S:20][C:21]=1[CH:22]=[O:23].[Cl-].[NH4+]>O1CCCC1.C(OCC)C.CCCCC.O>[CH3:6][C:7]1[N:8]=[CH:9][S:10][C:11]=1[CH:22]([C:21]1[S:20][CH:19]=[N:18][C:17]=1[CH3:16])[OH:23]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 5813394-Methylthiazole-5-carboxaldehydeHCID 116583544-Methyl-2-trimethylsilylthiazoleHCID 178418339Butyllithium

Product 1

HCID 22106674Bis(4-methyl-5-thiazolyl)methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 86634712Tetrahydrofuran ether pentaneSolvent

Procedure

n-Butyllithium (2.5M solution in hexanes, 12.8 ml) was added dropwise to a stirred solution of 4-methyl-2-trimethylsilylthiazole (5 g) in anhydrous tetrahydrofuran/diethyl ether/pentane (4:4:1, 75 ml) at -100° C. under an atmosphere of dry nitrogen. After 90 minutes, 4-methyl-5-thiazolecarbaldehyde (J. Amer. Chem. Soc., 1982, 104, 4934-4943) (4 g) was added. After a further 3 hours at -100° C., water was added and the mixture was warmed to room temperature. Saturated aqueous ammonium chloride solution was added and the organic phase was separated, dried and evaporated. The residue was crystallised from ethyl acetate to give bis(4-methyl-5-thiazolyl)methanol. This material in dichloromethane was oxidised using manganese dioxide to give the title compound.

Workup

  1. waitAfter a further 3 hours at -100° C.
  2. customthe organic phase was separated
  3. customdried
  4. customevaporated
  5. customThe residue was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-bf151e1ec0394f38bb4ec7d06729bbad
Source dataset
uspto-grants-1997_09
Patent number
US05665747

Reaction notes

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