(Trimethylsilyl)imidazole → Trimethyl{[(2s)-1,1,2-trimethyl-3-(phenylsulfonyl)propyl]oxy}silane

HRID 388731

반응식

HRID 388731 반응식
[CH3:1][C:2]([OH:16])([C@H:4]([CH3:15])[CH2:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH3:3].[CH3:17][Si:18]([CH3:25])([CH3:24])N1C=CN=C1>CN(C)C=O>[CH3:17][Si:18]([CH3:25])([CH3:24])[O:16][C:2]([CH3:1])([CH3:3])[C@H:4]([CH3:15])[CH2:5][S:6]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7]

참가 물질

4

반응물 2

HCID 28925(Trimethylsilyl)imidazoleHCID 13964863HCID 13964863, 화합물

생성물 1

HCID 68938726Trimethyl{[(2s)-1,1,2-trimethyl-3-(phenylsulfonyl)propyl]oxy}silane수율 96%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

The compound of Example 10B (0.95 g, 3.9 mmol) was dissolved in 3 mL of dimethylformamide; 1 mL of 1-(trimethylsilyl)imidazole was added, and the resultant solution was stirred overnight at ambient temperature, then heated at 80° C. for 8 hours. The crude mixture was partitioned between ethyl acetate and water; the organic phase was washed with brine and dried over Na2SO4. The solvents were removed in vacuo, and the residue was purified by chromatography on an Analogix Intelliflash 280™, eluting with a gradient of 0% to 20% ethyl acetate in hexanes to provide the titled compound (1.18 g, 96%).

후처리

  1. customThe crude mixture was partitioned between ethyl acetate and water
  2. washthe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvents were removed in vacuo
  5. customthe residue was purified by chromatography on an Analogix Intelliflash 280™
  6. washeluting with a gradient of 0% to 20% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-8baa344f47184079aa6489b993392493
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377913B2

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