Water → 2-(5-Bromopyridin-3-yl)ethan-1-ol

HRID 1253928ノート

反応式

HRID 1253928 の反応式
B#B.C1COCC1.[Br:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16](O)=[O:17])[CH:12]=[N:13][CH:14]=1.O>C1COCC1.C(OCC)(=O)C>[Br:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][OH:17])[CH:12]=[N:13][CH:14]=1

参加物

6

反応物 3

HCID 962WaterHCID 28025392-(5-Bromopyridin-3-yl)acetic acidHCID 131714434Diborane tetrahydrofuran

生成物 1

HCID 534036902-(5-Bromopyridin-3-yl)ethan-1-ol収率 23.9%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of Diborane-THF complex (1.0 M in THF, 7.5 mL, 7.5 mmol) was added dropwise to a solution of 5-bromo-3-pyridinylacetic acid (1080 mg, 5 mmol) in dry THF at 0° C. The resulting mixture was allowed to warm to room temperature. After 15 h, the reaction mixture was cooled to 0° C. and water (10 mL) was added dropwise. The reaction mixture was diluted with ethyl acetate (100 mL). The organic layer was separated, washed with brine, dried over Na2SO4. After filtration and concentration, the residue was purified by flash column and afforded of the title compound as colorless solid (241 mg). 1HNMR (CDCl3, 400.342 MHz) δ 2.89 (t, J=6 Hz, 2H), 3.92 (t, J=6 Hz, 3H), 7.99 (s, 1H), 8.46 (s, 1H), 8.60 (s, 1H).

後処理

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe residue was purified by flash column

出典と根拠

ORDレコード
ord-c1b90bd9127a4706905ad6980b1cac65
出典データセット
uspto-grants-2013_06
特許番号
US08455522B2

反応ノート

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