Ethanol → [4-(1,3-Thiazol-2-yl)phenyl]methanol

HRID 2359815Notes

Reaction equation

HRID 2359815 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1.C(O)C.O1CCCC1.[BH4-].[Na+]>O>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]([CH2:10][OH:11])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 105356554-(1,3-Thiazol-2-yl)benzaldehyde

Product 1

HCID 24229487[4-(1,3-Thiazol-2-yl)phenyl]methanolYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4-(thiazol-2-yl)benzaldehyde (see JP 2001-519414A) (1.57 g, 8.30 mmol) were added ethanol (20 ml), tetrahydrofuran (0.46 ml), and then sodium borohydride (157 mg, 4.15 mmol), followed by stirring at room temperature for 1.5 hours. After completion of the reaction, water was added to the reaction solution, followed by extraction with ethyl acetate. The separated organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=2:1→1:1 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (1.49 g) as a white solid. (Yield: 94%)

Workup

  1. additionwas added to the reaction solution
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additioncontaining the desired compound
  6. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-22af3ccd08ba4154aba665316c307938
Source dataset
uspto-grants-2014_04
Patent number
US08685986B2

Reaction notes

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