Boron trifluoride etherate → HCID 84732417、化合物

HRID 2277601ノート

反応式

HRID 2277601 の反応式
C([SiH](CC)CC)C.B(F)(F)F.CCOCC.[Cl:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:27])[NH:22][C:21]2(O)[CH3:28].[Cl:30][C:31]1[CH:39]=[C:38]2[C:34]([C:35](O)([CH3:41])[NH:36][C:37]2=[O:40])=[CH:33][CH:32]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:27])[NH:22][CH:21]2[CH3:28].[Cl:30][C:31]1[CH:39]=[C:38]2[C:34]([CH:35]([CH3:41])[NH:36][C:37]2=[O:40])=[CH:33][CH:32]=1

参加物

8

反応物 5

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 86685928HCID 86685928、化合物HCID 86685929HCID 86685929、化合物

生成物 2

HCID 847324166-Chloro-3-methylisoindolin-1-one収率 9.6%HCID 84732417HCID 84732417、化合物収率 11%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Under N2 protection, triethylsilane (23 g, 200 mmol) and trifluoroboron etherate (8.51 g, 60 mmol) were added successively at −15° C. to a mixture of 5-chloro-3-hydroxy-3-methyl-2,3-dihydro-isoindol-1-one and 6-chloro-3-hydroxy-3-methyl-2,3-dihydro-isoindol-1-one (3.95 g, 20 mmol) in dry DCM (100 mL). Afterwards, the reaction mixture was stirred at room temperature for 2 hours and a saturated aqueous solution of NaHCO3 (30 mL) was added. The mixture was then extracted with DCM and the organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude mixture of products. The two regioisomers were separated by prep-HPLC to give the title compounds, 5-chloro-3-methyl-2,3-dihydro-isoindol-1-one (0.4 g, 11%) and 6-chloro-3-methyl-2,3-dihydro-isoindol-1-one (0.35 g, 9.6%) as white solids. MS: 182.0 (M+H+).

後処理

  1. extractionThe mixture was then extracted with DCM
  2. washthe organic layer was washed with brine
  3. customdried over anhy
  4. filtrationNa2SO4, filtered
  5. concentrationconcentrated in vacuo
  6. customto give a crude
  7. additionmixture of products
  8. customThe two regioisomers were separated by prep-HPLC

出典と根拠

ORDレコード
ord-88c7f1e9b6ae42a2923650cd45745ea9
出典データセット
uspto-grants-2015_09
特許番号
US09133158B2

反応ノート

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