Methanol → HCID 86730205、化合物

HRID 57451ノート

反応式

HRID 57451 の反応式
[Cl:1][C:2]1[C:3]([C:13]([F:16])([F:15])[CH3:14])=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7](OCC)=[O:8].[Li+].[BH4-].CO>CCOCC>[Cl:1][C:2]1[CH:12]=[C:6]([CH2:7][OH:8])[CH:5]=[N:4][C:3]=1[C:13]([F:15])([F:16])[CH3:14]

参加物

5

反応物 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 86730206Ethyl 5-chloro-6-(1,1-difluoroethyl)nicotinate

生成物 1

HCID 86730205HCID 86730205、化合物収率 95.1%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
40 °C

実験手順

To a solution of ethyl 5-chloro-6-(1,1-difluoroethyl)nicotinate (2.68 g, 10.74 mmol) in Et2O (40 mL) was added LiBH4 (0.351 g, 16.10 mmol), followed by dropwise addition of methanol (0.653 mL, 16.10 mmol). The reaction was refluxed at 40° C. for one hour. The reaction mixture was then cooled to 0° C., and quenched with HCl (1M) until pH=2 for aqueous layer. The phases were separated and the aqueous layer was extracted with DCM (3×50 mL). The organic was then dried (Na2SO4) and concentrated under reduced pressure to give final crude product (2.12 g). LCMS m/z 208.0 (M+H)+, Rt 0.63 min.

後処理

  1. temperatureThe reaction mixture was then cooled to 0° C.
  2. customquenched with HCl (1M) until pH=2 for aqueous layer
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with DCM (3×50 mL)
  5. dry with materialThe organic was then dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-ec68920441b04f92af4b5a87376574ac
出典データセット
uspto-grants-2016_09
特許番号
US09434719B2

反応ノート

読み込み中…