3-Hydroxybenzaldehyde → 3-(1-Propenyl)phenol

HRID 129807

반응식

HRID 129807 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[OH:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=O.[CH2:20](OCC)[CH3:21]>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.C1COCC1>[CH:15]([C:14]1[CH:13]=[C:12]([OH:11])[CH:19]=[CH:18][CH:17]=1)=[CH:20][CH3:21]

참가 물질

6

반응물 3

HCID 1013-HydroxybenzaldehydeHCID 3283Diethyl EtherHCID 3251421Potassium bis(trimethylsilyl)amide

생성물 1

HCID 539593403-(1-Propenyl)phenol수율 93%

시약·촉매·용매 2

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

반응 조건

온도
0 °C

실험 절차

To a suspension of (ethyl)triphenylphosphonium bromide (35 g, 94.3 mmol) in THF (95 mL) was added potassium bis (trimethylsilyl)amide (180 ml, 0.5M in toluene, 90.2 mmol) dropwise. The reaction was stirred at 0° C. for 30 min, then a solution of 3-hydroxy-benzaldehyde (5 g, 41.0 mmol) in THF (5 mL) was added dropwise. After addition the reaction was stirred at 0° C. for 1 h. Ethyl ether (200 mL) was added to dilute the reaction. The organic layer was washed with water (50 mL×2), brine (50 mL×2) and dried over magnesium sulfate. Purification was performed by flash chromatography on 600 g silica gel, loaded and eluted with 10% ethyl acetate in hexane. Pure fractions were combined and evaporated to give the title compound (5.1 g, 93%) as a colorless oil.

후처리

  1. additionAfter addition the reaction
  2. stirringwas stirred at 0° C. for 1 h
  3. additionto dilute
  4. customthe reaction
  5. washThe organic layer was washed with water (50 mL×2), brine (50 mL×2)
  6. dry with materialdried over magnesium sulfate
  7. customPurification
  8. washeluted with 10% ethyl acetate in hexane
  9. customevaporated

출처 및 근거

ORD 기록
ord-e85e3f0ca5084a3fbcd0a85b8b987a7b
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05470845

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