Lithium borohydride → HCID 39347891、化合物

HRID 2366188ノート

反応式

HRID 2366188 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 39347891HCID 39347891、化合物収率 98%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

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+].

後処理

  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)

出典と根拠

ORDレコード
ord-0c45855672484b4b83590f18cd95fede
出典データセット
uspto-grants-2014_04
特許番号
US08697708B2

反応ノート

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