Suberic acid → Oct-4-enedioic acid

HRID 2196789

반응식

HRID 2196789 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 84313Oct-4-enedioic acid수율 71%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-414e95955aba4677bcdcae4ef5879452
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338478B2

연결된 노트

불러오는 중…