Tetrahydrofuran → 1-(2,4-Dimethylthiazol-5-yl)-2-methylpropan-1-ol

HRID 526831Notes

Reaction equation

HRID 526831 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH:8]=[O:9])=[C:5]([CH3:7])[N:6]=1.[CH2:10]1[CH2:14]OC[CH2:11]1>>[CH3:1][C:2]1[S:3][C:4]([CH:8]([OH:9])[CH:10]([CH3:14])[CH3:11])=[C:5]([CH3:7])[N:6]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 27762492,4-Dimethyl-1,3-thiazole-5-carbaldehyde

Product 1

HCID 1180063231-(2,4-Dimethylthiazol-5-yl)-2-methylpropan-1-ol

Procedure

A solution of 2,4-dimethylthiazole-5-carbaldehyde (1.07 g, 7.58 mmol) in THF (12 mL) was cooled to 0° C. Isopropyl magnesium chloride LiCl complex (1.3 M in THF, 6 mL, 8.8 mmol) was then added dropwise. After 30 minutes, the reaction mixture was quenched with aqueous NH4Cl solution and the aqueous portion was extracted with EtOAc (3×50 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to afford an orange oil. Chromatography on silica gel (5% acetone-DCM increasing to 30% acetone) provided the title compound as a light amber oil.

Workup

  1. customthe reaction mixture was quenched with aqueous NH4Cl solution
  2. extractionthe aqueous portion was extracted with EtOAc (3×50 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford an orange oil

Sources & evidence

ORD record
ord-9ef82d345a8f48f08bee4a0c1701a03f
Source dataset
uspto-grants-2016_05
Patent number
US09346782B2

Reaction notes

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