Saccharin → N-(6-tert-Butyldimethylsilyloxy-hexyl)saccharin

HRID 512019

反応式

HRID 512019 の反応式
[S:1]1([C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5](=[O:6])[NH:4]1)(=[O:3])=[O:2].[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>CN(C=O)C.O.CCOC(C)=O>[Si:23]([O:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:4]1[C:5](=[O:6])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[S:1]1(=[O:2])=[O:3])([C:26]([CH3:27])([CH3:28])[CH3:29])([CH3:25])[CH3:24]

参加物

7

反応物 3

HCID 5143SaccharinHCID 24758Sodium hydrideHCID 4260352(6-Bromohexyloxy)-tert-butyldimethylsilane

生成物 1

HCID 25018868N-(6-tert-Butyldimethylsilyloxy-hexyl)saccharin収率 45%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of saccharin (92 mg, 0.5 mmol) in anhydrous DMF (4 mL), at room temperature, under a nitrogen atmosphere, was added NaH (60% dispersion in mineral oil, 21 mg, 0.52 mmol). The mixture was stirred at the same temperature for additional 15 min, a solution of (6-bromohexyloxy)-tert-butyldimethylsilane (177 mg, 0.6 mmol) in DMF (1 mL) was added and the resulting mixture microwaved at 150° C. for 10 min. The reaction mixture was cooled to room temperature and diluted with water (5 mL) and AcOEt (10 mL). The organic layer was separated and the aqueous layer extracted with AcOEt (2×10 mL). The combined organic layer was washed with brine, dried (MgSO4) and the solvent removed in vacuum. The residue was purified by flash column chromatography on silica gel (20% ethyl acetate-petroleum ether) to give 83.8 (89 mg, 45% yield), as a viscous liquid.

後処理

  1. customthe resulting mixture microwaved at 150° C. for 10 min
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with AcOEt (2×10 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuum
  7. customThe residue was purified by flash column chromatography on silica gel (20% ethyl acetate-petroleum ether)

出典と根拠

ORDレコード
ord-b27bcf4747144841a9e1fa95fccda40d
出典データセット
uspto-grants-2015_08
特許番号
US09102622B2

関連ノート

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