Lithium borohydride → HCID 39347891, 화합물

HRID 2366188노트

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HRID 2366188 반응식
[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

참가 물질

4

반응물 2

HCID 4148881Lithium borohydrideHCID 668018164-Thiazolecarboxylic acid, 2-(2-chloro-6-fluorophenyl)-, ethyl ester

생성물 1

HCID 39347891HCID 39347891, 화합물수율 98%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

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+].

후처리

  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)

출처 및 근거

ORD 기록
ord-0c45855672484b4b83590f18cd95fede
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697708B2

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