Methanesulfonic Acid → Dimethyl (3-oxo-1,3-dihydro-2-benzofuran-1-yl)phosphonate

HRID 459754

반응식

HRID 459754 반응식
[P:1]([O-:6])([O:4][CH3:5])[O:2][CH3:3].C[O-].[Na+].[C:10]([C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=[O:16])(O)=[O:11].CS(O)(=O)=O>CO>[O:11]=[C:10]1[C:13]2[C:14](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]([P:1](=[O:6])([O:4][CH3:5])[O:2][CH3:3])[O:16]1

참가 물질

6

반응물 4

HCID 6395Methanesulfonic AcidHCID 8406Phthalaldehydic acidHCID 10942334Sodium MethoxideHCID 21884954Dimethylphosphite

생성물 1

HCID 11118213Dimethyl (3-oxo-1,3-dihydro-2-benzofuran-1-yl)phosphonate수율 90.3%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Dimethyl phosphite (100 g, 0.909 mol) was added dropwise at 0° C. under nitrogen to a stirred solution of sodium methoxide [from sodium (20.9 g, 0.909 gatom)] in methanol (730 ml), the mixture was stirred for 5 minutes, and 2-carboxybenzaldehyde (95.45 g, 0.64 mol) was added in portions. The stirred mixture was allowed to warm to ambient temperature, then it was stirred for 30 minutes and cooled in ice. Methanesulfonic acid (96 g, 1 mol) was added in portions at 5–10° C., then the solvent was removed in vacuo. The residue was partitioned between dichloromethane (1800 ml) and water (450 ml), and the organic layer was separated, washed with water (2×450 ml) and dried (MgSO4) The solvent was removed in vacuo, the residue was triturated with ether (150 ml), and the resulting solid was collected by filtration, washed with ether (30 ml) and dried in vacuo to give dimethyl 3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonate (139.94 g) as a white crystalline solid, m.pt 95–96.5° C.; 250 MHz 1H-nmr (d6-DMSO) δ (ppm): 3.65 (d, 3H) (—OCH3), 3.85 (d, 3H) (—OCH3), 6.4 (d, 1H) (—CH—P), 7.75 (m, 2H) (2×ArH), 7.85–8.05 (m, 2H) (2×ArH); m/z (M+H)+. 243, 100% purity.

후처리

  1. stirringit was stirred for 30 minutes
  2. temperaturecooled in ice
  3. customthe solvent was removed in vacuo
  4. customThe residue was partitioned between dichloromethane (1800 ml) and water (450 ml)
  5. customthe organic layer was separated
  6. washwashed with water (2×450 ml)
  7. dry with materialdried (MgSO4) The solvent
  8. customwas removed in vacuo
  9. customthe residue was triturated with ether (150 ml)
  10. filtrationthe resulting solid was collected by filtration
  11. washwashed with ether (30 ml)
  12. customdried in vacuo

출처 및 근거

ORD 기록
ord-6f6f8d0085474818a20bb04433cdd128
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196085B2

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