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

HRID 639031

반응식

HRID 639031 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 522689Potassium Fluoride용매

반응 조건

온도
70 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-d9d90dc5a40042f08d047cdbe41771eb
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691850B2

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