Citric Acid → (3,4-Dichloroisothiazol-5-yl)methanol

HRID 2236115Notes

Reaction equation

HRID 2236115 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:8]([Cl:9])=[C:7]([C:10](Cl)=[O:11])[S:6][N:5]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.C1COCC1>[Cl:3][C:4]1[C:8]([Cl:9])=[C:7]([CH2:10][OH:11])[S:6][N:5]=1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 109768863,4-Dichloro-5-isothiazolecarbonyl chloride

Product 1

HCID 16723166(3,4-Dichloroisothiazol-5-yl)methanolYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.9 g (50.5 mmol) of sodium borohydride was suspended in 40 ml of water. To the resulting suspension was dropwise added, at 10 to 15° C., a solution of the 3,4-dichloroisothiazole-5-carbonyl chloride dissolved in THF (4 ml). Stirring was conducted at 15° C. for 30 minutes. Then, an aqueous citric acid solution was added to make the mixture weakly acidic and extraction with ethyl acetate was conducted. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated. The resulting crystals were washed with hexane to obtain 3.0 g (yield: 81%) of (3,4-dichloroisothiazol-5-yl)methanol as colorless crystals (melting point: 94 to 95° C.).

Workup

  1. additionTo the resulting suspension was dropwise added, at 10 to 15° C.
  2. extractionextraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. washThe resulting crystals were washed with hexane

Sources & evidence

ORD record
ord-f759f7fdbe61436faad937c3fcb4c6cf
Source dataset
uspto-grants-2010_05
Patent number
US07714140B2

Reaction notes

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