methyl 4,5-dichloroisothiazole-3-carboxylate → HCID 66854171, compound

HRID 252110Notes

Reaction equation

HRID 252110 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:5]([C:10](OC)=[O:11])=[N:6][S:7][C:8]=1[Cl:9]>C(O)C>[Cl:3][C:4]1[C:5]([CH2:10][OH:11])=[N:6][S:7][C:8]=1[Cl:9]

Participants

4

Reactant 2

HCID 1244566methyl 4,5-dichloroisothiazole-3-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 66854171HCID 66854171, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add sodium borohydride (76 mg, 2.0 mmol) to methyl 4,5-dichloroisothiazole-3-carboxylate (212 mg, 1.0 mmol) in ethanol (10 mL) at room temperature and stir overnight. Add water, extract with dichloromethane three times. Combine the organic layers and wash with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give (4,5-dichloroisothiazol-3-yl)-methanol as a white solid (141 mg, 77%). 1H NMR (400 MHz, MeOH-d4) 4.66 (s, 2H).

Workup

  1. extractionAdd water, extract with dichloromethane three times
  2. washCombine the organic layers and wash with saturated aqueous sodium chloride
  3. dry with materialdry (magnesium sulfate)
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-48677cbd9f4c4fb7803ce53bc8d26e6d
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

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