2-Methyltetrahydrofuran → 6-(1,3-Dioxolan-2-ylmethyl)isochromen-1-one

HRID 1466112

反応式

HRID 1466112 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][CH:6]=[CH:5]2.F[B-](F)(F)F.C([PH+](CCCC)CCCC)CCC.Br[Zn][CH2:33][CH:34]1[O:38][CH2:37][CH2:36][O:35]1.CC1CCCO1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:35]1[CH2:36][CH2:37][O:38][CH:34]1[CH2:33][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][CH:6]=[CH:5]2

参加物

7

反応物 4

HCID 73012-MethyltetrahydrofuranHCID 11818592Tri-n-butylphosphonium tetrafluoroborateHCID 212520476-bromo-1H-isochromen-1-oneHCID 178419777HCID 178419777、化合物

生成物 1

HCID 772306596-(1,3-Dioxolan-2-ylmethyl)isochromen-1-one

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

A mixture of 6-Bromo-1H-isochromen-1-one (980 mg, 4.4 mmol), tributyl phosphonium tetrafluoroborate (25 mg, 0.087 mmol), palladium (II) acetate (9.8 mg, 0.044 mmol) was suspended in DMF (10 ml) then added bromo(1,3-dioxolan-2-ylmethyl)zinc (9.58 ml, 4.79 mmol) and purged with nitrogen. The reaction was heated to 85° C. for 10 hours and then stirred at RT overnight. Methyl tetrahydrofuran was added and the mixture was washed with brine. The organic layer was dried over MgSO4, filtered and evaporated to dryness. The residue was purified thru a 80 g ISCO Redi-sep column and eluted with 0-100% EtOAc/hexane to yield the title compound.

後処理

  1. washthe mixture was washed with brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was purified thru a 80 g ISCO Redi-sep column
  6. washeluted with 0-100% EtOAc/hexane

出典と根拠

ORDレコード
ord-0df325619bf04c4688296e944b0714f0
出典データセット
uspto-grants-2015_04
特許番号
US08999990B2

関連ノート

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