Potassium tert-butoxide → 4-Benzyloxy-2-[2-(4-methoxyphenyl)allyloxy]-1-vinylbenzene

HRID 254910Notes

Reaction equation

HRID 254910 reaction equation
[CH3:1]C([O-])(C)C.[K+].[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([CH:33]=[CH2:34])=[C:19]([CH:32]=1)[O:20][CH2:21][C:22]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([CH:33]=[CH2:34])=[C:19]([O:20][CH2:21][C:22]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)=[CH2:1])[CH:32]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 498213242-(5-Benzyloxy-2-vinylphenoxy)-1-(4-methoxyphenyl)ethanone

Product 1

HCID 595921064-Benzyloxy-2-[2-(4-methoxyphenyl)allyloxy]-1-vinylbenzeneYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of MTPPB (2.29 g, 6.41 mmol) in anhydrous THF (20 mL) was cooled in an ice bath and added with t-BuOK (0.72 g, 6.42 mmol) in portions under nitrogen. After stirring at 0° C. for 15 min, the suspension was added with compound 2a (2.0 g, 5.34 mmol) as obtained above. The resultant mixture was stirred at 0° C. for 2 hrs, followed by quenching with a saturated NH4Cl solution. After removal of most of the THF in vacuo, the resultant residue was extracted six times with EtOAc (20 mL). The organic layers were combined, washed with a saturated NaCl solution, and dried with anhydrous MgSO4. After filtration, the filtrate was concentrated in vacuo, followed by purification via silica gel column chromatography (ethyl acetate/n-hexane=1:15), thus giving the title compound 2 as a colorless liquid (1.89 g, 95% yield).

Workup

  1. temperaturewas cooled in an ice bath
  2. customas obtained above
  3. customby quenching with a saturated NH4Cl solution
  4. customAfter removal of most of the THF in vacuo
  5. extractionthe resultant residue was extracted six times with EtOAc (20 mL)
  6. washwashed with a saturated NaCl solution
  7. dry with materialdried with anhydrous MgSO4
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated in vacuo
  10. customfollowed by purification via silica gel column chromatography (ethyl acetate/n-hexane=1:15)

Sources & evidence

ORD record
ord-e8345f0968994aed8e7a640a2eaeed76
Source dataset
uspto-grants-2011_01
Patent number
US07875736B2

Reaction notes

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