Réaction #738227

Équation de réaction

Cyclohexylmethylmagnesium bromide

product

4-methylthiazole-5-carboxaldehyde

THF

→

title compound

Rendement 58.0%

4-methyl-5-(1-hydroxy-2-cyclohexylethyl)thiazole

Rendement 58.0%

Solvants

ether

Conditions de réaction

Traitement

1. 1
   Températurewarmed to room temperature
2. 2
   workup.STIRRINGstirred for an additional 3 hours
3. 3
   AutreThe reaction was quenched with 10 mL THF/1M HCl (1:1)
4. 4
   AutreThe aqueous and organic layers were separated
5. 5
   ExtractionThe aqueous layer was extracted with EtOAc (3×10 mL)
6. 6
   Lavagewashed with brine
7. 7
   Séchagedried (MgSO4)
8. 8
   Concentrationconcentrated under vacuum
9. 9
   AutreThe residue was purified by silica gel column (1:1 EtOAc/hexanes)

Mode opératoire

A 3-neck, 100 mL round-bottom flask was charged with the product from Example 22D (412.6 mg, 3.5 mmol) and anhydrous THF (15 mL) under N2 atmosphere. The reaction was cooled to −10° C. Cyclohexylmethylmagnesium bromide (7 mL, of a 1.0M solution in ether, 7 mmol) was added dropwise. The reaction was stirred for 1 hour, warmed to room temperature, and stirred for an additional 3 hours. The reaction was quenched with 10 mL THF/1M HCl (1:1). The aqueous and organic layers were separated. The pH ofthe aqueous layer was adjusted to 3 with 1M HCl. The aqueous layer was extracted with EtOAc (3×10 mL). All organic layers were combined and washed with brine, dried (MgSO4), and concentrated under vacuum. The residue was purified by silica gel column (1:1 EtOAc/hexanes) to provide 425.2 mg (58%) of the title compound as an orange oil.

Source