Isopropenyl acetate → HCID 14368623、化合物

HRID 1653835ノート

反応式

HRID 1653835 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([O:18][C:19]([CH3:21])=[CH2:20])(=O)C.C[O-].C([Sn+](CCCC)CCCC)CCC>C1(C)C=CC=CC=1.CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH2:20][C:19](=[O:18])[CH3:21])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1

参加物

6

反応物 3

HCID 7916Isopropenyl acetateHCID 27568764-Bromo-4'-chlorobiphenylHCID 11964040Methoxytri-n-butylstannane

生成物 1

HCID 14368623HCID 14368623、化合物収率 68.3%

試薬・触媒・溶媒 2

HCID 178424406HCID 178424406、化合物触媒HCID 1140Toluene溶媒

実験手順

To a stirred solution of 4-bromo-4'-chlorobiphenyl (16 g; F. R. Shaw and E. E. Turner. J. Chem. Soc., 285 (1932) ), isopropenyl acetate (9 g) and dichlorobis(tri-o-tolylphosphine)palladium (0.47 g) in dry toluene (30 ml), under nitrogen, was added tributyltin methoxide (25.9 ml; Aldrich). The mixture was stirred and heated at 100° for 5 hr, cooled and the solvent evaporated in vacuo. The residue was chromatographed on silica gel, eluting with cyclohexane then ether. The resultant solid was recrystallised from cyclohexane to afford the title compound (10 g), m.p. 79°-81°.

後処理

  1. temperatureheated at 100° for 5 hr
  2. temperaturecooled
  3. customthe solvent evaporated in vacuo
  4. customThe residue was chromatographed on silica gel
  5. washeluting with cyclohexane
  6. customThe resultant solid was recrystallised from cyclohexane

出典と根拠

ORDレコード
ord-e9b9488455b64804a38a0559ad86553b
出典データセット
uspto-grants-1995_04
特許番号
US05403934

反応ノート

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