2-Bromothiazole → 1211507-79-7

HRID 440325Notes

Reaction equation

HRID 440325 reaction equation
[Li]CCCC.Br[C:7]1[S:8][CH:9]=[CH:10][N:11]=1.[CH:12]1([CH:15]=[O:16])[CH2:14][CH2:13]1>CCOCC>[OH:16][CH:15]([C:7]1[S:8][CH:9]=[CH:10][N:11]=1)[CH:12]1[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 764302-BromothiazoleHCID 123114CyclopropanecarboxaldehydeHCID 178418339Butyllithium

Product 1

HCID 224069731211507-79-7Yield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

n-BuLi (26.7 mL, 42.8 mmol, 1.6M) was added dropwise to a -78° C. solution of 2-bromothiazole (6.7 g, 40.8 mmol) in dry Et2O (80 mL). After stirring at -78° C. for 1 h, cyclopropanal (32 mL, 42.8 mmol) was added and the solution stirred 30 min. The reaction was quenched with water, the layers separated and the aqueous extracted with EtOAc. The combined extracts were dried (MgSO4), and condensed. The crude material was purified by flash chromatography using 40% EtOAc/hexane to give 5.98 g (95%) of 2-(1-hydroxy-1-cyclopropylmethyl)thiazole as a yellow oil.

Workup

  1. stirringthe solution stirred 30 min
  2. customThe reaction was quenched with water
  3. customthe layers separated
  4. extractionthe aqueous extracted with EtOAc
  5. customThe combined extracts were dried
  6. custom(MgSO4), and condensed
  7. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-8b743ce7939d46f8aefb0adc7500f544
Source dataset
uspto-grants-1996_05
Patent number
US05519040

Reaction notes

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