Vanillic Acid → 4-(Nitrooxy)butyl 4-hydroxy-3-methoxybenzoate

HRID 1471413ノート

反応式

HRID 1471413 の反応式
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:20][CH2:21][CH2:22][CH2:23][O:24][N+:25]([O-:27])=[O:26]>CN(C)C=O.ClCCl>[OH:8][C:7]1[CH:9]=[CH:10][C:2]([C:1]([O:12][CH2:20][CH2:21][CH2:22][CH2:23][O:24][N+:25]([O-:27])=[O:26])=[O:11])=[CH:3][C:4]=1[O:5][CH3:6]

参加物

6

反応物 3

HCID 8468Vanillic AcidHCID 10796Cesium carbonateHCID 104202524-Bromobutyl nitrate

生成物 1

HCID 594073554-(Nitrooxy)butyl 4-hydroxy-3-methoxybenzoate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of vanillic acid (5.0 g, 29.73 mmol) in N,N-dimethylformamide (50 ml), cesium carbonate (9.68 g, 29.73 mmol) was added. The reaction was cooled at 0° C. and a 20% solution of 1-bromo-4-(nitrooxy)butane in dichloromethane (29.45 g) was added. The reaction was stirred at room temperature for 69 hours. The mixture was poured into a 5% aqueous NaH2PO4 solution and extracted with diethyl ether (3×70 ml) The organic layers were washed with water (70 ml), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (Biotage System, Cartridge column FLASH 65+M™ KP-Sil, eluent: gradient n-hexane/ethyl acetate 95/5 (500 ml), to n-hexane/ethyl acetate 1/1 during 4000 ml, n-hexane/ethyl acetate 1/1 (500 ml)). The product (5.88 g) was obtained.

後処理

  1. extractionextracted with diethyl ether (3×70 ml) The organic layers
  2. washwere washed with water (70 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (Biotage System, Cartridge column FLASH 65+M™ KP-Sil, eluent: gradient n-hexane/ethyl acetate 95/5 (500 ml), to n-hexane/ethyl acetate 1/1 during 4000 ml, n-hexane/ethyl acetate 1/1 (500 ml))

出典と根拠

ORDレコード
ord-95b5c92bbadf4422bd1652525808d689
出典データセット
uspto-grants-2015_04
特許番号
US09012435B2

反応ノート

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