Water → (2-Methylbenzo[D]thiazol-6-YL)methanol

HRID 594242Notes

Reaction equation

HRID 594242 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1[S:9][C:10]2[CH:16]=[C:15]([C:17](OCC)=[O:18])[CH:14]=[CH:13][C:11]=2[N:12]=1.O.[OH-].[Na+]>C1COCC1>[CH3:7][C:8]1[S:9][C:10]2[CH:16]=[C:15]([CH2:17][OH:18])[CH:14]=[CH:13][C:11]=2[N:12]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 640775Ethyl 2-methyl-1,3-benzothiazole-6-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 676590(2-Methylbenzo[D]thiazol-6-YL)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

A cooled (−10° C.) suspension of LiAlH4 (188 mg; 4.97 mmol) in anh. THF (30 ml) was treated with a solution of commercially available ethyl 2-methylbenzo[d]thiazole-6-carboxylate (1.000 g; 4.51 mmol) in anh. THF (20 ml). The mixture was further stirred at −10° C. for 20 min. Water (0.19 ml), 15% aq. NaOH (0.19 ml), and water (0.57 ml) were then successively added, and the resulting mixture was further stirred at rt for 1 h. Filtration, concentration to dryness under reduced pressure, and additional drying under HV afforded (2-methylbenzo[d]thiazol-6-yl)methanol as a yellow oil. LC-MS (conditions A): tR=0.45 min.; [M+H]+: 180.16 g/mol.

Workup

  1. temperatureA cooled
  2. stirringthe resulting mixture was further stirred at rt for 1 h
  3. filtrationFiltration, concentration to dryness under reduced pressure
  4. customadditional drying under HV

Sources & evidence

ORD record
ord-c19d53bb330d4aa8ab3521f69762e2fa
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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