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

HRID 446357노트

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HRID 446357 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-83adbfe4800f489680f918fbce8c926f
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476265B2

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