Ethyl phenylacetate → Ethyl 3-(2,3-dihydrobenzofuran-5-yl)-2-phenylpropionate

HRID 324635Notes

Reaction equation

HRID 324635 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C[Si](C)(C)N[Si](C)(C)C.C([Li])CCC.[C:25]1([CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Br[CH2:38][C:39]1[CH:40]=[CH:41][C:42]2[O:46][CH2:45][CH2:44][C:43]=2[CH:47]=1>O1CCCC1.O>[O:46]1[C:42]2[CH:41]=[CH:40][C:39]([CH2:38][CH:31]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:47][C:43]=2[CH2:44][CH2:45]1

Participants

8

Reactant 5

HCID 7590Ethyl phenylacetateHCID 13838HexamethyldisilazaneHCID 2733832Lithium HexamethyldisilazideHCID 220048075-(Bromomethyl)-2,3-dihydrobenzofuranHCID 178418339Butyllithium

Product 1

HCID 22004839Ethyl 3-(2,3-dihydrobenzofuran-5-yl)-2-phenylpropionate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of lithium hexamethyldisilazide solution, prepared from 1,1,1,3,3,3-hexamethyldisilazane (37.4 g, 0.232 mol), n-butyllithium (127 mL, 1.6M hexane solution) and tetrahydrofuran (150 mL), was added a solution of ethyl phenylacetate (33.3 g, 0.203 mol) in tetrahydrofuran (20 mL) at −78° C. The mixture was stirred for 15 minutes and then a solution of 5-bromomethyl-2,3-dihydrobenzofuran (41.0 g, 0.193 mol) in tetrahydrofuran (50 mL) was added. The mixture was stirred for further 20 minutes, diluted with water and warmed up to room temperature. The product was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to afford the title compound as an oily product (yield 54.5 g, 95%).

Workup

  1. stirringThe mixture was stirred for further 20 minutes
  2. extractionThe product was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-3d6826ed03c5471baa04dc25edced71e
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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