Acetone → HCID 15161038, compound

HRID 1535047Notes

Reaction equation

HRID 1535047 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:7][C:6]=2[CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[CH:26]=[CH2:27].CC(C)=O>CCCCCC>[CH2:27]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([CH2:10][CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:7][C:6]=2[CH:18]=1)[CH:26]=[CH2:25]

Participants

6

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 98812472-(2-phenylethyl)-2,3-dihydro-1-benzofuran-5-ol

Product 1

HCID 15161038HCID 15161038, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture 5-hydroxy-2-(2-phenylethyl)-2,3-dihydrobenzoruan, E5, (50 gm; 208 mmoles), potassium carbonate (55 gm; 400 mmoles), allyl bromide (48 gm; 400 mmoles) and acetone (500 mL) was refluxed for 18 hours. The mixture was cooled, diluted with hexane (250 mL) and filtered through celite. The filtrate was concentrated in vacuo and the residue chromatographed in silica gel using 10% ethylacetate in hexane as eluent to obtain 47.8 gm (82%) of 5-allyloxy-2-(2-phenylethyl)-2,3-dihydrobenzofuran E6 as an oil.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue chromatographed in silica gel using 10% ethylacetate in hexane as eluent

Sources & evidence

ORD record
ord-92dfe2cbfc724613ae1c26aca93887e5
Source dataset
uspto-grants-1992_02
Patent number
US05091533

Reaction notes

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