Water → (7-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

HRID 984483

反応式

HRID 984483 の反応式
[Br:1][C:2]1[CH:9]=[C:6](C=O)[C:5]([OH:10])=[CH:4][CH:3]=1.[CH2:11]([CH:13]1[O:15][CH2:14]1)Cl.C([O-])([O-])=[O:17].[K+].[K+].O>CN(C=O)C>[OH:17][CH2:14][CH:13]1[CH2:11][O:10][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=2[O:15]1

参加物

6

反応物 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 728635-Bromosalicylaldehyde

生成物 1

HCID 233965(7-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol収率 44%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a stirred solution of 5-bromosalicylaldehyde (5.0 g, 24.9 mmol), and epichlorohydrin (5.6 mL, 72.1 mmol) in 20 mL of DMF at 80° C. was added K2CO3 slowly in portions. The resulting mixture was then heated at 90° C. for 3 h. Reaction was then stopped, water was added, extracted with diethyl ether. The organic extracts were washed with water, brine, dried over Na2SO4, concentrated in vacuo. The residue was purified on a SiO2 flash column chromatography eluting with 15-30% EtOAc/hexanes to give 2.82 g (44%) of the title compound as colorless oil.

後処理

  1. customReaction
  2. extractionextracted with diethyl ether
  3. washThe organic extracts were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on a SiO2 flash column chromatography
  7. washeluting with 15-30% EtOAc/hexanes

出典と根拠

ORDレコード
ord-1dc99065235e46769bedd783d4257b57
出典データセット
uspto-grants-2005_03
特許番号
US06867203B2

関連ノート

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