1,3-Thiazole-2-carbaldehyde → HCID 22406940, compound

HRID 440335Notes

Reaction equation

HRID 440335 reaction equation
[Li]CCCC.[CH3:6][O:7][CH2:8][O:9][CH2:10][Sn](CCCC)(CCCC)CCCC.[CH:24]([C:26]1[S:27][CH:28]=[CH:29][N:30]=1)=[O:25]>C1COCC1.O>[OH:25][CH:24]([C:26]1[S:27][CH:28]=[CH:29][N:30]=1)[CH2:10][O:9][CH2:8][O:7][CH3:6]

Participants

6

Reactant 3

HCID 27349031,3-Thiazole-2-carbaldehydeHCID 4193592Tributyl[(methoxymethoxy)methyl]stannaneHCID 178418339Butyllithium

Product 1

HCID 22406940HCID 22406940, compoundYield 34.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

n-BuLi (2.87 mmol, 1.8 mL, 1.6M) was added dropwise to a -78° C. solution of (methoxymethoxymethyl)tributyl tin (1.05 g, 2.87 mmol) in dry THF (10 mL). After stirring for 30 minutes a solution of 2-formylthiazole (2.73 mmol, 0.31 g) in THF (2 mL) was added and the solution stirred overnight. The reaction was diluted with water and extracted with ethyl acetate, dried (MgSO4), filtered and concentrated. The residue was subjected to flash chromatography (45% ethyl acetate/hexane) to afford 0.18 g (34%) of 2-(1-hydroxy-2-(methoxymethoxy)ethyl)thiazole.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7ea8db782fff4c0eb5e688272d25a0ea
Source dataset
uspto-grants-1996_05
Patent number
US05519040

Reaction notes

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