Sodium Chloride → 5-Acetylspiro(benzofuran-2(3H),1'-cyclopropan)-3-one

HRID 1065648Notes

Reaction equation

HRID 1065648 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:11]2[CH2:16][CH2:15][O:14][C:12]2=O)=[C:6](C(OC)=O)[CH:5]=1)(=[O:3])[CH3:2].[Cl-].[Na+]>C1CCN2C(=NCCC2)CC1.CN(C)C=O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:10][C:11]3([C:12](=[O:14])[C:8]=2[CH:9]=1)[CH2:16][CH2:15]3)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 13329388alpha-[(4-Acetyl-2-methoxycarbonylphenyl)oxy]-gamma-butyrolactone

Product 1

HCID 717555-Acetylspiro(benzofuran-2(3H),1'-cyclopropan)-3-oneYield 56.5%

Reagents, catalysts & solvents 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of α-[(4-acetyl-2-methoxycarbonylphenyl)oxy]-γ-butyrolactone (2.8 g), 1,8-diazabicyclo[5,4,0]-7-undecene (0.056 g), sodium chloride (0.6 g) and N,N-dimethylformamide (28 ml) was heated at 150°-155° C. for 4 hours. The solvent was removed in vacuo and the resulting residue was dissolved in ethyl acetate. The ethyl acetate solution was washed with water and dried. The residue obtained by removal of the solvent in vacuo was chromatographed on silica gel. The fraction eluted with dichloromethane was crystallized from ethanol to give 5-acetylspiro[benzo[b]furan-2(3H), 1'-cyclopropane]-3-one (1.15 g) as colorless crystals.

Workup

  1. temperaturewas heated at 150°-155° C. for 4 hours
  2. customThe solvent was removed in vacuo
  3. dissolutionthe resulting residue was dissolved in ethyl acetate
  4. washThe ethyl acetate solution was washed with water
  5. customdried
  6. customThe residue obtained by removal of the solvent in vacuo
  7. customwas chromatographed on silica gel
  8. washThe fraction eluted with dichloromethane
  9. customwas crystallized from ethanol

Sources & evidence

ORD record
ord-371449cc749442c681ca790909c3edc5
Source dataset
uspto-grants-1982_05
Patent number
US04330554

Reaction notes

Loading…