3,5-Dimethoxybenzaldehyde → 3,5-Dimethoxy-1-(1-propenyl)benzene

HRID 24700

반응식

HRID 24700 반응식
[Li][CH2:2][CH2:3]CC.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([O:16][CH3:17])[CH:15]=1)[CH:11]=O>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.C1COCC1>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:2][CH3:3])[CH:13]=[C:14]([O:16][CH3:17])[CH:15]=1

참가 물질

5

반응물 2

HCID 817473,5-DimethoxybenzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 539005613,5-Dimethoxy-1-(1-propenyl)benzene

시약·촉매·용매 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

Ethyltriphenylphosphonium bromide (4.69 g) was dissolved in anhydrous THF (70 mL) and the mixture cooled to 0-5° C. n-BuLi (5.05 mL of 2.5 M in hexane) was added dropwise and the resulting mixture was stirred at room temperature for 3 h. The mixture was cooled to −78° C. and a solution of 3,5-dimethoxybenzaldehyde (2 g) in anhydrous THF (14 mL) was added. The mixture was allowed to warm up to room temperature then stirred overnight. The mixture was concentrated, and the residue was taken up with AcOEt, washed with water and brine, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (silica gel; eluent: hexane and AcOEt 10:1) to give 3,5-dimethoxy-1-(1-propenyl)benzene as a mixture of cis and trans isomers (2.15 g).

후처리

  1. additionwas added dropwise
  2. temperatureThe mixture was cooled to −78° C.
  3. temperatureto warm up to room temperature
  4. stirringthen stirred overnight
  5. concentrationThe mixture was concentrated
  6. washwashed with water and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column chromatography (silica gel; eluent: hexane and AcOEt 10:1)

출처 및 근거

ORD 기록
ord-e4d69c828dae4568959d5d61d5b064ec
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855843B2

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