Ethyl Acetate → Benzo[d]thiazol-5-ylmethanol

HRID 408574Notes

Reaction equation

HRID 408574 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[S:12][CH:11]=[N:10][C:9]=2[CH:13]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOC(C)=O.[OH-].[Na+]>C1COCC1.O>[S:12]1[C:8]2[CH:7]=[CH:6][C:5]([CH2:3][OH:2])=[CH:13][C:9]=2[N:10]=[CH:11]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22610014Methyl benzo[d]thiazole-5-carboxylate

Product 1

HCID 22281733Benzo[d]thiazol-5-ylmethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a −78° C. cooled solution of benzothiazole-5-carboxylic acid methyl ester (1 eq.) in dry THF under nitrogen was slowly added a solution of LiAlH4 (1M in THF, 1.5 eq.). The reaction was stirred at −78° C. for 2 h, then warmed to 20° C. EtOAc was added to the reaction, then aqueous NaOH (2N) and finally water. The reaction mixture was stirred at 20° C. for 30 min, then filtered through a pad of celite. The filtrate was concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 1/0 to 1/1) to afford benzothiazol-5-yl-methanol.

Workup

  1. temperaturewarmed to 20° C
  2. stirringThe reaction mixture was stirred at 20° C. for 30 min
  3. filtrationfiltered through a pad of celite
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 1/0 to 1/1)

Sources & evidence

ORD record
ord-5ec3223b9a1741fdbed9a6908a9e31e4
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Reaction notes

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