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

HRID 1065648노트

반응식

HRID 1065648 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene촉매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-371449cc749442c681ca790909c3edc5
출처 데이터셋
uspto-grants-1982_05
특허 번호
US04330554

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