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

HRID 1675329Notes

Reaction equation

HRID 1675329 reaction equation
[BH4-].[Na+].C1COCC1.[Cl:8][C:9]1[C:13]([Cl:14])=[C:12]([C:15](Cl)=[O:16])[S:11][N:10]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O>[Cl:8][C:9]1[C:13]([Cl:14])=[C:12]([CH2:15][OH:16])[S:11][N:10]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 109768863,4-Dichloro-5-isothiazolecarbonyl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

1.9 g (50.5 mmol) of sodium borohydride was suspended in 40 ml of water. To the suspension was dropwise added, at 10 to 15° C., a THF (4 ml) solution of the above-produced 3,4-dichloroisothiazole-5-carbonyl chloride. The mixture was stirred at 15° C. for 30 minutes. Then, an aqueous citric acid solution was added to the mixture to make it weakly acidic, followed by extraction with ethyl acetate. 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 suspension was dropwise added, at 10 to 15° C.
  2. extractionfollowed by extraction 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-76bf26aaece64b1eaee4d2d4e8fc0df4
Source dataset
uspto-grants-2011_08
Patent number
US08003675B2

Reaction notes

Loading…