Water → (3-fluorophenyl)(pyridin-2-yl)methanol

HRID 443426ノート

反応式

HRID 443426 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[F:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=[O:18].O>CCOCC.CCCCCCC>[F:13][C:14]1[CH:15]=[C:16]([CH:17]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[OH:18])[CH:19]=[CH:20][CH:21]=1

参加物

7

反応物 4

HCID 962WaterHCID 79732-BromopyridineHCID 680093-FluorobenzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 23467199(3-fluorophenyl)(pyridin-2-yl)methanol

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒3 回HCID 8900Heptane溶媒

反応条件

温度
-40 °C

実験手順

A solution of 17.4 g of 2-bromopyridine in 40 ml of ether is added slowly with stirring to 75 ml of commercial n-butyl lithium in heptane and 100 ml of ether at -50° to -40° C. under a nitrogen atmosphere. After stirring another 0.25 hours at -40° C., a solution of 12.5 g of 3-fluorobenzaldehyde in 30 ml of ether is added dropwise and the mixture is allowed to warm to room temperature. After stirring 3 hours, 100 ml of water is added, the organic layer is separated, dried over MgSO4 and the solvent is evaporated. The residue is chromatographed over silica gel in acetonitrile to obtain alpha-(3-fluorophenyl)-2-pyridinemethanol; mp 80°-82° C., after recrystallization from cyclohexane. The alpha-(3-fluorophenyl)-2-pyridinemethanol is hydrogenated at about 50 lbs. p.s.i. in methanol-acetic acid in the presence of 10% Rh/C. The reaction mixture is filtered, the solvent evaporated from the filtrate, and the residue dissolved in methylene dichloride and shaken with concentrated sodium hydroxide. The organic layer is separated, dried, and concentrated to obtain the desired alpha-(3-fluorophenyl)-2-piperidinemethanol; mp 146°-148° C.

後処理

  1. temperatureto warm to room temperature
  2. stirringAfter stirring 3 hours
  3. customthe organic layer is separated
  4. dry with materialdried over MgSO4
  5. customthe solvent is evaporated
  6. customThe residue is chromatographed over silica gel in acetonitrile

出典と根拠

ORDレコード
ord-fd7992e9a99346d197a13c11aa075c49
出典データセット
uspto-grants-1981_04
特許番号
US04260623

反応ノート

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