Dimethylformamide → 5-(1,1-Dimethyl-allyl)-2-methoxy-benzaldehyde

HRID 1989818노트

반응식

HRID 1989818 반응식
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:12])([CH3:11])[CH:9]=[CH2:10])[CH:5]=[CH:4][C:3]=1[O:13][CH3:14].[Li]CCCC.CN([CH:23]=[O:24])C>C1COCC1>[CH3:11][C:8]([C:6]1[CH:5]=[CH:4][C:3]([O:13][CH3:14])=[C:2]([CH:7]=1)[CH:23]=[O:24])([CH3:12])[CH:9]=[CH2:10]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 112422612-Bromo-4-(1,1-dimethyl-allyl)-1-methoxy-benzeneHCID 178418339Butyllithium

생성물 1

HCID 113331815-(1,1-Dimethyl-allyl)-2-methoxy-benzaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

To a solution of 2-Bromo-4-(1,1-dimethyl-allyl)-1-methoxy-benzene (3.1 g, 0.012 mol) in dry THF (50 mL) was cooled to −78° C. under argon. n-BuLi (2.5M, 5.1 mL, 0.0128 mol) was added keeping the temperature below −70° C. The yellow mixture was stirred for another 15 min and quenched with dry DMF (1.4 mL, 0.018 mol). The cooling bath was removed and the mixture was allowed to warm to 25° C. A saturated solution of NaHCO3 (30 mL) was added and then extracted with EtOAc (3×50 mL). The organic phase was dried (Na2SO4) and evaporated to yellow oil. Yield: 2.31 g (94%).

후처리

  1. customthe temperature below −70° C
  2. customThe cooling bath was removed
  3. additionA saturated solution of NaHCO3 (30 mL) was added
  4. extractionextracted with EtOAc (3×50 mL)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customevaporated to yellow oil

출처 및 근거

ORD 기록
ord-ada405e7b3eb4dd8838b9f85449f6475
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07642367B2

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