Water → HCID 118131408, 화합물

HRID 634426노트

반응식

HRID 634426 반응식
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][O:2]1.O=P(Cl)(Cl)Cl.C(#N)C.O.[CH2:21]([Cl:23])Cl>CN(C=O)C.C(O)=O>[Cl:23][C:21]1[C:9]2[C:10](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:1][O:2][C:3]=1[CH:4]=[O:11]

참가 물질

8

반응물 5

HCID 962WaterHCID 6342AcetonitrileHCID 6344Dichloromethane2회HCID 24813Phosphorus oxychlorideHCID 123396483,4-dihydro-1H-2-benzopyran-4-one

생성물 1

HCID 118131408HCID 118131408, 화합물수율 60.6%

시약·촉매·용매 2

HCID 284Formic Acid용매HCID 6228Dimethylformamide용매

실험 절차

To commercially available isochroman-4-one (900 mg, 6.07 mmol) in DCM (18 ml), DMF (0.706 ml) and POCl3 (1.699 ml, 18.23 mmol) were added in sequence under Nitrogen at r.t. The mixture was refluxed for 6 h and kept at r.t overnight. The reaction mixture was diluted with DCM (15 ml), washed with water and sat NaCl, then anhydrified over Na2SO4 and evaporated in vacuo. The resulting crude was purified via reverse phase chromatography with a Biotage C18 SNAP 30 g column (Phase A, water 95%, ACN 5%, formic acid 0.1%); Phase B ACN 95%, water 5%, formic acid 0.1%) to give 4-chloro-1H-isochromene-3-carbaldehyde (Intermediate G20.1, 716 mg, 60.6% yield)

후처리

  1. temperatureThe mixture was refluxed for 6 h
  2. washwashed with water
  3. customevaporated in vacuo
  4. customThe resulting crude was purified via reverse phase chromatography with a Biotage C18 SNAP 30 g column (Phase A, water 95%, ACN 5%, formic acid 0.1%)

출처 및 근거

ORD 기록
ord-a40045dd22b54889abc0668bac39b539
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321776B2

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