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

HRID 1065648ノート

反応式

HRID 1065648 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene触媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-371449cc749442c681ca790909c3edc5
出典データセット
uspto-grants-1982_05
特許番号
US04330554

反応ノート

読み込み中…