Tetrahydrofuran → 1,1'-{[4-(Prop-1-en-2-yl)-1,3-phenylene]bis(oxymethylene)}dibenzene

HRID 2097285노트

반응식

HRID 2097285 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1[C:23](=O)[CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1[C:23]([CH3:24])=[CH2:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 8028Tetrahydrofuran2회HCID 3194691-(2,4-Bis(benzyloxy)phenyl)ethanone

생성물 1

HCID 247733591,1'-{[4-(Prop-1-en-2-yl)-1,3-phenylene]bis(oxymethylene)}dibenzene

시약·촉매·용매 1

HCID 74505Methyltriphenyliphosphonium bromide촉매

실험 절차

Methyltriphenylphosphonium bromide (1.1 eq) was suspended in an. THF and cooled to 0° C. under nitrogen. 1.6M nButyllithium in hexanes (1.1 eq) was added drop wise, and stirred for 30 minutes. 1-(2,4-Bis-benzyloxy-phenyl)-ethanone (1 eq) was dissolved in an. THF and added drop wise to the suspension. When addition was completed, the ice bath was removed and the reaction mixture was stirred at room temperature under nitrogen overnight. Methanol was added to the reaction mixture and the resulting solution was evaporated in vacuo. Hexane was added to the resulting oil and heated to reflux for 30 minutes, then filtered through Celite. The liquor was evaporated in vacuo to give an oil which was purified by column chromatography, eluting with 30% EtOAc in hexane, to give 2,4-Bis-benzyloxy-1-isopropenyl-benzene. Rf retention time 0.722, 3:1 Hexane:EtOAc.

후처리

  1. additionWhen addition
  2. customthe ice bath was removed
  3. stirringthe reaction mixture was stirred at room temperature under nitrogen overnight
  4. additionMethanol was added to the reaction mixture
  5. customthe resulting solution was evaporated in vacuo
  6. additionHexane was added to the resulting oil
  7. temperatureheated
  8. temperatureto reflux for 30 minutes
  9. filtrationfiltered through Celite
  10. customThe liquor was evaporated in vacuo
  11. customto give an oil which
  12. customwas purified by column chromatography
  13. washeluting with 30% EtOAc in hexane

출처 및 근거

ORD 기록
ord-b633d72ff1894bbb8b8739fbdcf9303a
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450310B2

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