2-Bromopyridine → HCID 21187637、化合物

HRID 969562ノート

反応式

HRID 969562 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[CH2:13]1[O:23][C:16]2([CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]2)[O:15][CH2:14]1>CCOCC>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:19]1([OH:22])[CH2:20][CH2:21][C:16]2([O:23][CH2:13][CH2:14][O:15]2)[CH2:17][CH2:18]1

参加物

5

反応物 3

HCID 79732-BromopyridineHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418339Butyllithium

生成物 1

HCID 21187637HCID 21187637、化合物収率 33.6%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of 2-bromopyridine (14 g, 88.6 mmol) in anhydrous ether (300 mL) cooled at −78° C. was slowly added a solution of 2.5 M n-butyl lithium (36 mL). After the addition, stirring was continued at −78° C. for 1 hour. To it was slowly added a solution of 1,4-cyclohexanedione mono-ethylene ketal (15 g, 96 mmol) in anhydrous ether (300 mL). When the addition was complete, the mixture was allowed to warm to 0° C. and stirring was continued for 1 hour. The reaction was quenched by addition of an aqueous solution (100 mL) of ammonium chloride (4.5 g). The organic phase was separated and the aqueous phase was extracted with methylene chloride 4 times. The combined organic phases were dried over MgSO4 and concentrated. Crystallization from EtOAc provided 7 g of the desired product. The mother liquid was purified on silica gel eluting with 10% MeOH/EtOAc to give another 3 g of the desired product. MS calculated for C13H17NO3: (M+H)+236; found 236.0.

後処理

  1. additionAfter the addition
  2. additionWhen the addition
  3. stirringstirring
  4. waitwas continued for 1 hour
  5. customThe reaction was quenched by addition of an aqueous solution (100 mL) of ammonium chloride (4.5 g)
  6. customThe organic phase was separated
  7. extractionthe aqueous phase was extracted with methylene chloride 4 times
  8. dry with materialThe combined organic phases were dried over MgSO4
  9. concentrationconcentrated
  10. customCrystallization from EtOAc

出典と根拠

ORDレコード
ord-cefe049422504858a4581852c5ecd00c
出典データセット
uspto-grants-2007_12
特許番号
US07307086B2

反応ノート

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