Acetone → 2,2-dimethyl-4-oxo-4H-1,3-benzodioxine-6-carbonitrile

반응식

[C:1]([C:3]1[CH:11]=[C:7]([C:8]([OH:10])=[O:9])[C:6]([OH:12])=[CH:5][CH:4]=1)#[N:2].C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.[CH3:26][C:27]([CH3:29])=O>>[CH3:26][C:27]1([CH3:29])[O:12][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:11][C:7]=2[C:8](=[O:10])[O:9]1

참가 물질

반응물 3

HCID 180Acetone2회

HCID 9845Trifluoroacetic anhydride

HCID 130269355-Cyano-2-hydroxybenzoic acid

생성물 1

HCID 597024522,2-dimethyl-4-oxo-4H-1,3-benzodioxine-6-carbonitrile수율 15%

실험 절차

To a suspension of 5-cyano salicylic acid (60 g, 0.368 mol) in TEA (134 mL, 1.76 mol) and TFAA (45 mL, 0.32 mol) was added dry acetone (20 mL) and heated to reflux. After each 1 h interval was added 15 mL of dry acetone for 4 times and the reflux continued for 20 h. The reaction mixture was concentrated under vacuum and crude purified by flash column chromatography over silica gel (230-400 mesh) using CH2Cl2 as an eluent to give the title compound as a white solid (12 g, 15%). TLC: CH2Cl2 (100%), Rf: 0.5

후처리

temperatureheated to reflux
concentrationThe reaction mixture was concentrated under vacuum and crude
custompurified by flash column chromatography over silica gel (230-400 mesh)

출처 및 근거

ORD 기록: ord-3373f06d6e1e43daac4605bad0b0ee54
출처 데이터셋: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07365225B2

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