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

反応式

[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

参加物

反応物 3

HCID 180Acetone2 回

HCID 9845Trifluoroacetic anhydride

HCID 130269355-Cyano-2-hydroxybenzoic acid

生成物 1

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

実験手順

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

後処理

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

出典と根拠

ORDレコード: ord-3373f06d6e1e43daac4605bad0b0ee54
出典データセット: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07365225B2

反応ノート

読み込み中…

参加物