Sodium borohydride → HCID 12953373, compound

HRID 354728Notes

Reaction equation

HRID 354728 reaction equation
[Cl:1][C:2]1[S:3][C:4]([C:10]([O-])=[O:11])=[C:5]([CH:7]([CH3:9])[CH3:8])[N:6]=1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[S:3][C:4]([CH2:10][OH:11])=[C:5]([CH:7]([CH3:9])[CH3:8])[N:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20505778HCID 20505778, compound

Product 1

HCID 12953373HCID 12953373, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 8.0 g (0.034 mol) of ethyl, 2-chloro-4-isopropyl-5-thiazolecarboxylate and 20 ml of ethanol was added 1.3 g (0.034 mol) of sodium borohydride in 10 minutes. The reaction mixture was stirred at room temperature for 30 minutes and concentrated under reduced pressure. The residue was chromatographed on 250 g of silica gel using ether petroleum ether (1:9, v/v) as eluant. The first fraction (2.2 g) was recovered starting material. The second fraction (3.4 g) was Kugelrohr distilled at 0.5 mm (pot temperature 95° C.) go give 2.7 g (40%) of 2-chloro-4-isopropyl-5-thiazolemethanol as a colorless liquid, nD25 1.5425.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was chromatographed on 250 g of silica gel
  3. customThe first fraction (2.2 g) was recovered
  4. distillationdistilled at 0.5 mm (pot temperature 95° C.)

Sources & evidence

ORD record
ord-35099ea6c9d049b3ac17c17dad4c55d5
Source dataset
uspto-grants-1983_03
Patent number
US04377054

Reaction notes

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