3-Allyl-4-allyloxy-5-methoxybenzoic acid → 9-Methoxy-2,5-dihydrobenzo[b]oxepine-7-carboxylic acid

HRID 638910

반응식

HRID 638910 반응식
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([O:17][CH3:18])[C:12]=1[O:13][CH2:14][CH:15]=[CH2:16])[C:7]([OH:9])=[O:8])C=C>C(Cl)Cl.CCOC(C)=O.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1C=CC(C=[Ru](Cl)Cl)=CC=1>[CH3:18][O:17][C:11]1[C:12]2[O:13][CH2:14][CH:15]=[CH:16][CH2:1][C:4]=2[CH:5]=[C:6]([C:7]([OH:9])=[O:8])[CH:10]=1

참가 물질

5

반응물 1

HCID 686852123-Allyl-4-allyloxy-5-methoxybenzoic acid

생성물 1

HCID 686881349-Methoxy-2,5-dihydrobenzo[b]oxepine-7-carboxylic acid수율 100.3%

시약·촉매·용매 3

HCID 11967259Benzylidenebis(tricyclohexylphosphine)dichlororuthenium촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of 3-allyl-4-allyloxy-5-methoxybenzoic acid (200 mg, 0.81 mmol) in CH2Cl2 (20 mL) at room temperature was added benzylidene-bis-(tricyclohexylphosphine)dichlororuthenium (Grubb's catalyst, 35 mg, 0.04 mmol, 0.05 eq.). After stirring for 2 h the reaction was diluted with EtOAc (150 mL) then extracted with 2.0 N NaOH (100 mL). Aqueous layer was treated with brine (100 mL) then acidified to pH 5 using 1.0 N HCl. The aqueous layer was then extracted with EtOAc (2×200 mL). The organic layer was dried over MgSO4 and then concentrated in vacuo to afford 9-methoxy-2,5-dihydrobenzo[b]oxepine-7-carboxylic acid (179 mg, 100%) which was used without further purification.

후처리

  1. extractionthen extracted with 2.0 N NaOH (100 mL)
  2. additionAqueous layer was treated with brine (100 mL)
  3. extractionThe aqueous layer was then extracted with EtOAc (2×200 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b4a45f6ff79c48638c49dc1b87b003f3
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691843B2

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