Dimethylformamide → 3-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorobenzaldehyde

HRID 446362

反応式

HRID 446362 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][CH:29]=[CH:28][C:27]=1[F:32])([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[C:27]([F:32])=[C:28]([CH:29]=[CH:30][CH:31]=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 57988979tert-Butyl(2-fluorophenethoxy)dimethylsilaneHCID 178418339Butyllithium

生成物 1

HCID 579891643-(2-(tert-Butyldimethylsilyloxy)ethyl)-2-fluorobenzaldehyde

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A solution of 2,2,6,6-tetramethylpiperidine (11.0 g) in anhydrous THF (200 mL) was cooled to −78° and treated with butyllithium (37.5 mL), added steadily over 5 minutes via a syringe. The solution was stirred at −78° for 15 minutes and then treated with a solution of tert-butyl(2-fluorophenethoxy)dimethylsilane [Aromatic Intermediate 5, step a] (9.9 g) in THF (25 mL), added dropwise over 15 minutes. The solution that was stirred at −78° for 2 hours, then treated with a solution of DMF (9.0 mL) in THF (25 mL), added dropwise over 10 minutes. The solution was stirred at −78° for 1 hour, then the cooling bath was removed and the solution was allowed to warm to room temperature overnight. The reaction mixture was poured into aqueous HCl (0.5M) and extracted three times with ethyl acetate. The combined organic phases were washed three times with water, once with brine, then dried over magnesium sulphate, filtered and concentrated under reduced pressure to afford the titled compound. Yield 10.1 g.

後処理

  1. additionadded steadily over 5 minutes via a syringe
  2. additionadded dropwise over 15 minutes
  3. stirringThe solution that was stirred at −78° for 2 hours
  4. additionadded dropwise over 10 minutes
  5. stirringThe solution was stirred at −78° for 1 hour
  6. customthe cooling bath was removed
  7. additionThe reaction mixture was poured into aqueous HCl (0.5M)
  8. extractionextracted three times with ethyl acetate
  9. washThe combined organic phases were washed three times with water
  10. dry with materialonce with brine, then dried over magnesium sulphate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-5cf6efee4ae1477bac80d10aedbcc7cf
出典データセット
uspto-grants-2013_07
特許番号
US08476265B2

関連ノート

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