Dimethylformamide → 8-Methyl-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde

HRID 639031ノート

反応式

HRID 639031 の反応式
Br[C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=[C:4]([CH:12]=[O:13])[CH:3]=1.[CH3:14]N(C=O)C>[F-].[K+]>[CH3:14][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=[C:4]([CH:12]=[O:13])[CH:3]=1

参加物

4

反応物 2

HCID 6228DimethylformamideHCID 166371768-Bromo-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde

生成物 1

HCID 451220228-Methyl-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde収率 83%

試薬・触媒・溶媒 1

HCID 522689Potassium Fluoride溶媒

反応条件

温度
70 °C

実験手順

To a solution of 8-bromo-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde (240 mg, 0.987 mmol) in DMF (5 mL) were added LiCL (126 mg, 2.96 mmol), Me Sn (0.137 mL, 0.987 mmol) and PdCL2(PPh)2 (35 mg, 0.049 mmol). After heated at 70° C. for 12 hr, the mixture was cooled down to room temperature and diluted with aqueous KF solution. The resulting solution was extracted several times with DCM. The organic parts were combined, concentrated and purified with column chromatography (silica, 10-40% Ethyl acetate in hexane) affording the title compound as an off-white solid (145 mg, 83%): MS (ES) m/z 179 (M+H)+.

後処理

  1. temperaturethe mixture was cooled down to room temperature
  2. extractionThe resulting solution was extracted several times with DCM
  3. concentrationconcentrated
  4. custompurified with column chromatography (silica, 10-40% Ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-d9d90dc5a40042f08d047cdbe41771eb
出典データセット
uspto-grants-2010_04
特許番号
US07691850B2

反応ノート

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