Diisobutylaluminum hydride → 1375097-86-1

HRID 594226Notes

Reaction equation

HRID 594226 reaction equation
[S:1]1[CH:5]=[C:4]([C:6]2[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=2)[C:9](OCC)=[O:10])[N:3]=[CH:2]1.CC(C[AlH]CC(C)C)C.[OH-].[Na+].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.O>[S:1]1[CH:5]=[C:4]([C:6]2[CH:7]=[C:8]([CH2:9][OH:10])[CH:14]=[CH:15][CH:16]=2)[N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 14487Diisobutylaluminum hydrideHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 69082460HCID 69082460, compound

Product 1

HCID 690857541375097-86-1

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A cooled (−78° C.) solution of ethyl 3-(thiazol-4-yl)benzoate (501 mg; 2.14 mmol) in anh. toluene (7 ml) was treated with a solution of 1 M DIBAH in toluene (6.44 ml; 6.44 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 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 AcOEt (2×50 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-(thiazol-4-yl)phenyl)methanol as a pale yellow oil. LC-MS (conditions A): tR=0.50 min.; [M+H]+: 192.04 g/mol.

Workup

  1. waitat 0° C. for 30 min
  2. extractionThe separated aq. layer was further extracted with AcOEt (2×50 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-25faa28344ec4dfe99b993809654174f
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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