Hydrochloric Acid → 5-(Trimethylsilyl)thiazole-2-carboxaldehyde

HRID 1107728Notes

Reaction equation

HRID 1107728 reaction equation
C([Li])CCC.[CH3:6][Si:7]([CH3:14])([CH3:13])[C:8]1[S:12][CH:11]=[N:10][CH:9]=1.[CH:15](N1CCOCC1)=[O:16].Cl>C1COCC1>[CH3:6][Si:7]([CH3:14])([CH3:13])[C:8]1[S:12][C:11]([CH:15]=[O:16])=[N:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 20417N-FormylmorpholineHCID 27608675-TrimethylsilylthiazoleHCID 178418339Butyllithium

Product 1

HCID 187857825-(Trimethylsilyl)thiazole-2-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (1.50M in hexane, 39 mmol, 22 ml) was added dropwise at -78° C. to a solution of 5-(trimethylsilyl)thiazole (A. Dondoni et al, J. Org. Chem, 1988, 53, 1748) (5.2 g, 33 mmol) in THF (40 ml). After 30 min. a solution of N-formylmorpholine (4.57 g) in THF (40 ml) was added dropwise over 15 min. The resulting red solution was stirred a further 30 mi. and then allowed to warm to room temperature , dilute d with 4N hydrochloric acid and extracted three times with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride, dried over sodium sulphate and evaporated to leave a brown oil (5.5 g). M+ 185; 360 MHz 1H n.m.r (CDCl3) 9.89 (1H, s), 7.95 (1H, s), 0.24 (9H, s).

Workup

  1. additiondilute
  2. extractionextracted three times with ethyl acetate
  3. washThe combined extracts were washed with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-798d997de2cf4a24b17311f08bb588e7
Source dataset
uspto-grants-2000_05
Patent number
US06063789

Reaction notes

Loading…