2,6-Lutidine → ((1-(4-Bromophenyl)hexyl)oxy)(tert-butyl)dimethylsilane

HRID 15003

反応式

HRID 15003 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]([CH:23](O)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:19][CH:18]=1.N1C(C)=CC=CC=1C.C(=O)(O)[O-].[Na+]>ClCCl>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:19][CH:18]=1

参加物

6

反応物 4

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 516892Sodium BicarbonateHCID 126030861-(4-Bromophenyl)hexan-1-ol

生成物 1

HCID 57438973((1-(4-Bromophenyl)hexyl)oxy)(tert-butyl)dimethylsilane収率 88.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

TBSOTf (2.9 mL, 12.6 mmol) was added to an ice-cold solution of 4 (3.017 g, 11.7 mmol) and 2,6-lutidine (1.6 mL, 13.7 mmol) in dichloromethane (30 mL). The reaction was stirred for 2 h at room temperature and then 100 mL saturated sodium bicarbonate solution was added. The resulting mixture was extracted with dichloromethane (30 mL) and the dichloromethane layer was washed with 1 M HCl (2×50 mL) and brine (50 mL). The dichloromethane solution was then dried (MgSO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel (hexanes) gave compound 5 (3.843 g, 88%).

後処理

  1. extractionThe resulting mixture was extracted with dichloromethane (30 mL)
  2. washthe dichloromethane layer was washed with 1 M HCl (2×50 mL) and brine (50 mL)
  3. dry with materialThe dichloromethane solution was then dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification of the residue by flash chromatography on silica gel (hexanes)

出典と根拠

ORDレコード
ord-57b752c626fb4e7bb2cebf81a4fdcceb
出典データセット
uspto-grants-2010_06
特許番号
US07732443B2

関連ノート

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