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

HRID 1466112

반응식

HRID 1466112 반응식
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

참가 물질

7

반응물 4

HCID 73012-MethyltetrahydrofuranHCID 11818592Tri-n-butylphosphonium tetrafluoroborateHCID 212520476-bromo-1H-isochromen-1-oneHCID 178419777HCID 178419777, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
85 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0df325619bf04c4688296e944b0714f0
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999990B2

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