Dimethylformamide → 5-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorobenzaldehyde

HRID 446357ノート

反応式

HRID 446357 の反応式
CC1(C)CCCC(C)(C)N1.C([Li])CCC.[C:16]([Si:20]([O:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)([CH3:22])[CH3:21])([CH3:19])([CH3:18])[CH3:17].CN([CH:36]=[O:37])C>C1COCC1>[Si:20]([O:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[C:28]([CH:27]=1)[CH:36]=[O:37])([C:16]([CH3:19])([CH3:17])[CH3:18])([CH3:21])[CH3:22]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 130352,2,6,6-TetramethylpiperidineHCID 57989254tert-Butyl(4-fluorophenethoxy)dimethylsilaneHCID 178418339Butyllithium

生成物 1

HCID 579890665-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorobenzaldehyde

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of 2,2,6,6-tetramethylpiperidine (10.77 g) in THF (200 mL) at 0° C. was added over 25 minutes butyllithium (1.6M in hexanes, 48 mL). The mixture was cooled to −78° C. and a solution of tert-butyl(4-fluorophenethoxy)dimethylsilane [Aromatic Intermediate 3, step a] (9.7 g) in THF (50 mL) was added dropwise over 25 minutes. The reaction mixture was stirred at −78° C. for 90 minutes. DMF (9.3 mL) was then added dropwise over 10 minutes. The reaction mixture was stirred at 0° C. for 1 hour and then poured into ice-cold aqueous HCl (0.5M, 500 mL). The mixture was extracted with ethyl acetate and the organic layer washed twice with water, dried, filtered and the solvent concentrated under reduced pressure to give the subtitled compound. Yield 10.00 g.

後処理

  1. stirringThe reaction mixture was stirred at 0° C. for 1 hour
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer washed twice with water
  4. customdried
  5. filtrationfiltered
  6. concentrationthe solvent concentrated under reduced pressure

出典と根拠

ORDレコード
ord-83adbfe4800f489680f918fbce8c926f
出典データセット
uspto-grants-2013_07
特許番号
US08476265B2

反応ノート

読み込み中…