2-(2-Methoxy-6-vinylphenoxy)but-3-enyl 4-methylbenzenesulfonate → 8-methoxy-2H-1-benzopyran-2-methanol 4-methylbenzenesulfonate

HRID 902289노트

반응식

HRID 902289 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]([O:16][C:17]2[C:22]([CH:23]=[CH2:24])=[CH:21][CH:20]=[CH:19][C:18]=2[O:25][CH3:26])C=C)(=[O:10])=[O:9])=[CH:4][CH:3]=1>ClCCl.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1C=CC(C=[Ru](Cl)Cl)=CC=1>[CH3:26][O:25][C:18]1[C:17]2[O:16][CH:13]([CH2:12][OH:11])[CH:24]=[CH:23][C:22]=2[CH:21]=[CH:20][CH:19]=1.[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O-:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1

참가 물질

4

반응물 1

HCID 597015862-(2-Methoxy-6-vinylphenoxy)but-3-enyl 4-methylbenzenesulfonate

생성물 1

HCID 1317268418-methoxy-2H-1-benzopyran-2-methanol 4-methylbenzenesulfonate수율 183.5%

시약·촉매·용매 2

HCID 11967259Benzylidenebis(tricyclohexylphosphine)dichlororuthenium촉매HCID 6344Dichloromethane용매

실험 절차

A solution of 2-(2-methoxy-6-vinylphenoxy)but-3-enyl 4-methylbenzenesulfonate (4.4 g, 12 mmol) in dichloromethane (100 mL) was treated with benzylidene-bis(tricyclohexylphosphine)dichlororuthenium (0.9 g) at 23° C. with stirring. After 4 hours, the solvent volume was reduced under reduced pressure (to ca. 10 mL) and the solution was pre-adsorbed on silica gel (5 g). Purification by flash chromatography using a solvent gradient of 10 to 20% ethyl acetate in hexane provided 8-methoxy-2H-1-benzopyran-2-methanol 4-methylbenzenesulfonate (4.0 g, 98%) as a dark oil. MS (ESI) m/z 345.0 ([M−H]−).

후처리

  1. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-ffe8c4d44d0f4701b79ff7778ac5c435
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365095B2

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