Water → HCID 118131408、化合物

HRID 634426ノート

反応式

HRID 634426 の反応式
[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]

参加物

8

反応物 5

HCID 962WaterHCID 6342AcetonitrileHCID 6344Dichloromethane2 回HCID 24813Phosphorus oxychlorideHCID 123396483,4-dihydro-1H-2-benzopyran-4-one

生成物 1

HCID 118131408HCID 118131408、化合物収率 60.6%

試薬・触媒・溶媒 2

HCID 284Formic Acid溶媒HCID 6228Dimethylformamide溶媒

実験手順

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)

後処理

  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%)

出典と根拠

ORDレコード
ord-a40045dd22b54889abc0668bac39b539
出典データセット
uspto-grants-2016_04
特許番号
US09321776B2

反応ノート

読み込み中…