Suberic acid → Oct-4-enedioic acid

HRID 2196789

反応式

HRID 2196789 の反応式
[C:1]([OH:12])(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9].C(N(C(C)C)CCC(C1C=C(COC(=O)CCC=C)C=CC=1OC(=O)CCC=C)C1C=CC=CC=1)(C)C>ClCCl>[C:1]([OH:12])(=[O:11])[CH2:2][CH2:3][CH:4]=[CH:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9]

参加物

4

反応物 2

HCID 10457Suberic acidHCID 17874072(+/-)-Pent-4-enoic acid 2-(3-diisopropylamino-1-phenylpropyl)-4-(pent-4-enoyloxymethyl)phenyl ester

生成物 1

HCID 84313Oct-4-enedioic acid収率 71%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Intramolecular cyclic diester of octane-1,8-dioic acid and 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethyl-phenol Grubbs catalyst (benzylidene-bis-(tricyclohexylphosphine)-dichlororuthenium, 16 mg, 0.002 mmol, 2 mol-%) was added to a solution of (±)-pent-4-enoic acid 2-(3-diisopropylamino-1-phenylpropyl)-4-(pent-4-enoyloxymethyl)-phenyl ester (483 mg, 0.96 mmol) in dichloromethane (150 ml) and the mixture was refluxed for 96 hrs. under an atmosphere of nitrogen gas, after which all of the starting material was consumed as indicated by tlc. The mixture was filtered through a short pad of basic alumina, and the solvent was removed in vacuum. Flash chromatography (solvent system (4)) afforded the intermediate intramolecular cyclic diester of oct-4-ene-1,8-dioic acid and 2-(3-diisopropylamino)-1-(phenylpropyl)-4-hydroxymethyl-phenol (324 mg) as a colourless syrup (tlc: (4) Rf 0.68) in 71% yield, mixture of two geometrical isomers.

後処理

  1. temperaturethe mixture was refluxed for 96 hrs
  2. customunder an atmosphere of nitrogen gas, after which all of the starting material was consumed
  3. filtrationThe mixture was filtered through a short pad of basic alumina
  4. customthe solvent was removed in vacuum

出典と根拠

ORDレコード
ord-414e95955aba4677bcdcae4ef5879452
出典データセット
uspto-grants-2012_12
特許番号
US08338478B2

関連ノート

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