1,3-Thiazole-5-carbaldehyde → HCID 22013962, compound

HRID 1532865Notes

Reaction equation

HRID 1532865 reaction equation
[S:1]1[C:5]([CH:6]=[O:7])=[CH:4][N:3]=[CH:2]1.[CH:8]1([CH2:14][CH2:15][Mg]Br)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>C1COCC1.C(OCC)C>[S:1]1[C:5]([CH:6]([OH:7])[CH2:15][CH2:14][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 27735771,3-Thiazole-5-carbaldehydeHCID 178419672HCID 178419672, compound

Product 1

HCID 22013962HCID 22013962, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of thiazole-5-carboxaldehyde (2.31 g, 20.4 mmol) in 20 mL of in THF was added to a cold (0° C.) solution of 2-cyclohexylethylmagnesium bromide (prepared from 2-bromoethylcyclohexane (7.88 g) and magnesium turnings (1.22 g)) in 30 mL of ethyl ether and the mixture stirred 30 minutes. The cold bath was removed and the mixture stirred for 2 hours more and then quenched by the addition of 3N aqueous HCl. The solution was stirred until 2 clear phases resulted and then the layers were separated. The pH of the aqueous phase was adjusted to 4 with 2M aqueous sodium carbonate and then extracted with 3 portions of ethyl acetate. All the organic phases were combined and washed with brine, dried, filtered and concentrated. The residue was purified by column chromatography on silica gel (125 g, 50% ethyl acetate/hexanes) to provide 2.69 g (58%) of the title compound.

Workup

  1. customThe cold bath was removed
  2. stirringthe mixture stirred for 2 hours more
  3. customquenched by the addition of 3N aqueous HCl
  4. stirringThe solution was stirred until 2 clear phases
  5. customresulted
  6. customthe layers were separated
  7. extractionextracted with 3 portions of ethyl acetate
  8. washwashed with brine
  9. customdried
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified by column chromatography on silica gel (125 g, 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-686d227bda764e72875772395e37a0d5
Source dataset
uspto-grants-2001_03
Patent number
US06204293B1

Reaction notes

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