Sodium Chloride → Spiro(benzofuran-2(3H),1'-cyclopropan)-3-one, 7-acetyl-

HRID 1065647Notes

Reaction equation

HRID 1065647 reaction equation
[C:1]([C:4]1[C:9]([O:10][CH:11]2[CH2:16][CH2:15]OC2=O)=[C:8]([C:17]([O:19]C)=O)[CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C1CCN2C(=NCCC2)CC1.[Cl-].[Na+]>CN(C)C=O>[C:1]([C:4]1[C:9]2[O:10][C:11]3([C:17](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH2:16][CH2:15]3)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13037298alpha-[(6-Acetyl-2-methoxycarbonylphenyl)oxy]-gamma-butyrolactone

Product 1

HCID 3059949Spiro(benzofuran-2(3H),1'-cyclopropan)-3-one, 7-acetyl-Yield 8.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of α-[(6-acetyl-2-methoxycarbonylphenyl)oxy]-γ-butyrolactone (3.5 g), 1,8-diazabicyclo[5,4,0]-7-undecene (0.14 g) and sodium chloride (1.1 g) in N,N-dimethylformamide (66.5 ml) was stirred at 150°-160° C. for 5 hours. The solvent was distilled off under reduced pressure and the residue was subjected to chromatography on silica gel. The fraction eluted with dichloromethane was recrystallized from CHCl3 -hexane to give 7-acetylspiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one (0.22 g) as colorless needles melting at 114°-115° C.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. washThe fraction eluted with dichloromethane
  3. customwas recrystallized from CHCl3 -hexane

Sources & evidence

ORD record
ord-8bd8e1e30f524b24b7fdc50b0d89e4e1
Source dataset
uspto-grants-1982_05
Patent number
US04330554

Reaction notes

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