Triethylamine → [1-(4-Bromo-phenyl)-cyclobutoxy]-tert-butyl-dimethyl-silane

HRID 9234

反応式

HRID 9234 の反応式
[Si:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2(O)[CH2:26][CH2:25][CH2:24]2)=[CH:19][CH:18]=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>ClCCl>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:26][CH2:25][CH2:24]2)=[CH:19][CH:18]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 516892Sodium BicarbonateHCID 120954191-(4-Bromophenyl)cyclobutanol

生成物 1

HCID 21985972[1-(4-Bromo-phenyl)-cyclobutoxy]-tert-butyl-dimethyl-silane収率 93%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

TBSOTf (360 μL, 1.57 mmol) was added to a 0° C. solution of 3-1 (235 mg, 1.04 mmol) and triethylamine (450 μL, 3.23 mmol) in dichloromethane (3 mL). The reaction was allowed to warm to room temperature and after 1 h, saturated NaHCO3 solution was added. The resulting mixture was extracted with ethyl acetate (3×30 mL) and the combined ethyl acetate solution was washed with brine. The solution was then dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (hexanes) gave 3-2 (329 mg, 93%).

後処理

  1. extractionThe resulting mixture was extracted with ethyl acetate (3×30 mL)
  2. washthe combined ethyl acetate solution was washed with brine
  3. dry with materialThe solution was then dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography on silica gel (hexanes)

出典と根拠

ORDレコード
ord-3369d74bfe9e4f18bb09dcce8d3f401e
出典データセット
uspto-grants-2006_08
特許番号
US07091231B2

関連ノート

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