Water → (2-Methylbenzo[d]thiazol-5-yl)methanol

HRID 594245Notes

Reaction equation

HRID 594245 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1[S:9][C:10]2[CH:16]=[CH:15][C:14]([C:17](OC)=[O:18])=[CH:13][C:11]=2[N:12]=1.O.[OH-].[Na+]>C1COCC1>[CH3:7][C:8]1[S:9][C:10]2[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][C:11]=2[N:12]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 10910723Methyl 2-methyl-5-benzothiazolecarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2341868(2-Methylbenzo[d]thiazol-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

A cooled (−10° C.) suspension of LiAlH4 (207 mg; 5.47 mmol) in anh. THF (40 ml) was treated with a solution of methyl 2-methylbenzo[d]thiazole-5-carboxylate (1.032 g; 4.97 mmol) in anh. THF (20 ml). The mixture was further stirred at −10° C. for 20 min. Water (0.20 ml), 15% aq. NaOH (0.20 ml), and water (0.60 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-5-yl)methanol as a yellow oil. LC-MS (conditions A): tR=0.48 min.; [M+H]+: 180.19 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-681e00e109f141e496dc900da1aedee6
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

Loading…