Dimethylformamide → 4-(4,5-Dihydro-4,4-dimethyl-2-oxazolyl)-benzaldehyde

HRID 1057398노트

반응식

HRID 1057398 반응식
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][CH2:15][C:16]([CH3:19])([CH3:18])[N:17]=2)=[CH:9][CH:8]=1.CN(C)[CH:22]=[O:23]>O1CCCC1>[CH3:18][C:16]1([CH3:19])[CH2:15][O:14][C:13]([C:10]2[CH:11]=[CH:12][C:7]([CH:22]=[O:23])=[CH:8][CH:9]=2)=[N:17]1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 4033952-(4-Bromophenyl)-4,4-dimethyl-4,5-dihydrooxazoleHCID 178418339Butyllithium

생성물 1

HCID 125653984-(4,5-Dihydro-4,4-dimethyl-2-oxazolyl)-benzaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

n-Butyl lithium (9.44 ml, 2.5N solution in hexanes) was added to a solution of 2-(4-bromophenyl)-4,5-dihydro-4,4-dimethyl-oxazole [A. I. Meyers et al., J.O.C., 1974, 39, 2787] (5 g) in tetrahydrofuran (80 ml) at −78° C. The reddish solution was stirred at −78° C. for 15 minutes before dimethylformamide (2.3 g) was added dropwise. The resulting deep red solution was allowed to warm to room temperature, quenched with ammonium chloride solution and extracted into ether. The combined extracts were washed with brine, dried (sodium sulphate) and evaporated to dryness in vacuo. The residue was purified by column chromatography (30% ethyl acetate/hexane) to afford the title compound as a colourless liquid, 3.01 g.

후처리

  1. customat −78° C
  2. additionwas added dropwise
  3. customquenched with ammonium chloride solution
  4. extractionextracted into ether
  5. washThe combined extracts were washed with brine
  6. dry with materialdried (sodium sulphate)
  7. customevaporated to dryness in vacuo
  8. customThe residue was purified by column chromatography (30% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-caef90a330f34d1795057a9997bc21b3
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06514975B1

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