Sodium Bicarbonate → (4,6-Dimethyl-1,2-benzisothiazol-3-yl)-methanol

HRID 2175179Notes

Reaction equation

HRID 2175179 reaction equation
C[O:2][C:3]([C:5]1[C:9]2[C:10]([CH3:15])=[CH:11][C:12]([CH3:14])=[CH:13][C:8]=2[S:7][N:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O-])(O)=O.[Na+]>C1COCC1>[CH3:15][C:10]1[C:9]2[C:5]([CH2:3][OH:2])=[N:6][S:7][C:8]=2[CH:13]=[C:12]([CH3:14])[CH:11]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 584974334,6-Dimethyl-benzo[d]isothiazole-3-carboxylic acid methyl ester

Product 1

HCID 58497417(4,6-Dimethyl-1,2-benzisothiazol-3-yl)-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,6-dimethyl-benzo[d]isothiazole-3-carboxylic acid methyl ester (100 mg, 0.45 mmol) in THF (10 mL) was added lithium aluminum hydride (LiAlH4) (34 mg, 0.9 mmol) at 0° C. under nitrogen atmosphere. The solution was stirred at the same temperature for 1 hour. Sat. NaHCO3 was added and the solution was extracted with EtOAc. The combined organic layer was dried with MgSO4 and filtered. The filtrate was concentrated and the residue was used in the next step of the synthesis without further purification.

Workup

  1. extractionthe solution was extracted with EtOAc
  2. dry with materialThe combined organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe residue was used in the next step of the synthesis without further purification

Sources & evidence

ORD record
ord-ce99b2d8efa3433e97c3397acf4e1d3c
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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