Acetaldehyde → 1-(2-Chloro-8-fluoroquinolin-3-yl)ethanol

HRID 216809ノート

反応式

HRID 216809 の反応式
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([F:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([N-]C(C)C)(C)C.[Li+].[CH:21](=[O:23])[CH3:22]>C1COCC1>[Cl:1][C:2]1[C:11]([CH:21]([OH:23])[CH3:22])=[CH:10][C:9]2[C:4](=[C:5]([F:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

参加物

5

反応物 3

HCID 177AcetaldehydeHCID 2724682Lithium diisopropylamideHCID 221251942-Chloro-8-fluoroquinoline

生成物 1

HCID 577079711-(2-Chloro-8-fluoroquinolin-3-yl)ethanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

2-Chloro-8-fluoroquinoline (182 mg, 1.0 mmol) was dissolved in THF (2 mL) and cooled to −78° C. To this solution was added Lithium diisopropylamide (1M solution in THF, 1.1 mL, 1.1 mmol, 1.1 eq). The reaction was allowed to stir at −78° C. for 20 min, after which time acetaldehyde (113 μl, 2.0 mmol, 2 eq.) was added via syringe. After 30 minutes, the reaction was quenched with water and diluted with ethyl acetate. The layers were separated and washed with brine. The crude reaction mixture was purified by column chromatography (8:2 hexanes:ethyl acetate) to afford 1-(2-chloro-8-fluoroquinolin-3-yl)ethanol. 1H NMR (400 MHz, CDCl3) δ ppm 8.43 (br s, 1H), 7.64 (td, J=7.8, 5.1 Hz, 1H), 7.41 (ddd, J=10.2, 7.4, 1.2 Hz, 1H), 5.39 (qdd, J=6.3, 3.9, 0.8 Hz, 1H), 2.22 (d, J=3.9 Hz, 1H), 1.62 (d, J=6.3 Hz, 3H).

後処理

  1. waitAfter 30 minutes
  2. customthe reaction was quenched with water
  3. additiondiluted with ethyl acetate
  4. customThe layers were separated
  5. washwashed with brine
  6. customThe crude reaction mixture
  7. customwas purified by column chromatography (8:2 hexanes:ethyl acetate)

出典と根拠

ORDレコード
ord-3608627d884144e48aa7404a3aaaa955
出典データセット
uspto-grants-2012_06
特許番号
US08193199B2

反応ノート

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