Diisobutylaluminum hydride → (3-(5-Methylthiazol-2-yl)phenyl)methanol

HRID 594232Notes

Reaction equation

HRID 594232 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=2)[C:10](OCC)=[O:11])=[N:4][CH:3]=1.CC(C[AlH]CC(C)C)C.[OH-].[Na+].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.O>[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[C:9]([CH2:10][OH:11])[CH:15]=[CH:16][CH:17]=2)=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 14487Diisobutylaluminum hydrideHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 69085699Ethyl 3-(5-methylthiazol-2-yl)benzoate

Product 1

HCID 53273734(3-(5-Methylthiazol-2-yl)phenyl)methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A cooled (−78° C.) solution of ethyl 3-(5-methylthiazol-2-yl)benzoate (388 mg; 1.57 mmol) in anh. toluene (4 ml) was treated with a solution of 1 M DIBAH in toluene (4.71 ml; 4.71 mmol), and the resulting mixture was further stirred at −78° C., under nitrogen, for 5 min., and then at 0° C. for 30 min. The obtained mixture was then treated successively with water (35 ml), 1 M aq. NaOH (11 ml), and aq. sat. NaHCO3 (30 ml). The separated aq. layer was further extracted with Et2O (2×100 ml). The mixed organic layers were then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=20/1) afforded (3-(5-methylthiazol-2-yl)phenyl)methanol as a pale yellow oil. LC-MS (conditions A): tR=0.58 min.; [M+H]+: 206.01 g/mol.

Workup

  1. waitat 0° C. for 30 min
  2. extractionThe separated aq. layer was further extracted with Et2O (2×100 ml)
  3. dry with materialThe mixed organic layers were then dried over anh. MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customPurification by FC (DCM/MeOH=20/1)

Sources & evidence

ORD record
ord-3bf78f7d1daa4db09e1a0a03a7f3d68b
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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