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

HRID 646499Notes

Reaction equation

HRID 646499 reaction equation
[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

Participants

4

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 3194691-(2,4-Bis(benzyloxy)phenyl)ethanone

Product 1

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

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8618737e53d74841be0764266869de1f
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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