Lithium borohydride → HCID 66801740, compound

HRID 2366167Notes

Reaction equation

HRID 2366167 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[S:10][CH:11]=[C:12]([C:14](OCC)=[O:15])[N:13]=1.[BH4-].[Li+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[S:10][CH:11]=[C:12]([CH2:14][OH:15])[N:13]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 66801659HCID 66801659, compound

Product 1

HCID 66801740HCID 66801740, compoundYield 103.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of ethyl 2-(2,6-dichlorophenyl)thiazole-4-carboxylate (7.0 g, 23 mmol) in MeOH (100 mL) was added lithium borohydride (0.98 g, 47 mmol) in four portions. After addition, the mixture was stirred at 0° C. for 1 hour. The reaction mixture was quenched with water (100 mL) and extracted with EtOAc (3×100 mL). The combined organic extract was washed with brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified via silica gel column chromatography eluting with EtOAc/petroleum ether (1:5) to give the desired product as a white solid (6.2 g, 97% yield). 1H NMR (DMSO-d6, 500 MHz): δ 7.74 (s, 1H), 7.66-7.64 (m, 2H), 7.60-7.56 (m, 1H), 5.52 (t, J=5.5 Hz, 1H), 4.70 (m, 2H). LCMS (ESI) m/z: 260.1 [M+H+].

Workup

  1. additionAfter addition
  2. customThe reaction mixture was quenched with water (100 mL)
  3. extractionextracted with EtOAc (3×100 mL)
  4. extractionThe combined organic extract
  5. washwas washed with brine (100 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified via silica gel column chromatography
  9. washeluting with EtOAc/petroleum ether (1:5)

Sources & evidence

ORD record
ord-42fad82db6144f5d8027abc36e193c4a
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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