Lithium borohydride → HCID 39347891, compound

HRID 2366188Notes

Reaction equation

HRID 2366188 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F: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]([F: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 668018164-Thiazolecarboxylic acid, 2-(2-chloro-6-fluorophenyl)-, ethyl ester

Product 1

HCID 39347891HCID 39347891, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of ethyl 2-(2-chloro-6-fluorophenyl)thiazole-4-carboxylate (7.0 g, 25 mmol) in MeOH (100 mL) was added lithium borohydride (1.62 g, 73.8 mmol) in four portions. After addition, the resulting mixture was stirred at 0° C. for 1 hour. The 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 (5.8 g, 98% yield). 1H NMR (500 MHz, DMSO-d6): δ 7.74 (s, 1H), 7.35-7.41 (m, 1H) NOT ENOUGH AR PROTONS, 5.47 (s, 1H), 4.67 (m, 2H). LCMS (ESI) m/z: 244.1 [M+H+].

Workup

  1. additionAfter addition
  2. customThe 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-0c45855672484b4b83590f18cd95fede
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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