Imidazole → tert-butyl(dimethyl)silyl [(2R)-6-iodo-3,4-dihydro-2H-chromen-2-yl]methyl ether

HRID 47672

反応式

HRID 47672 の反応式
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C@@H:7]([CH2:12][OH:13])[CH2:6][CH2:5]2.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].N1C=CN=C1.O>CN(C=O)C>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C@@H:7]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:6][CH2:5]2

参加物

6

反応物 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 9943850[(2R)-6-iodo-3,4-dihydro-2H-chromen-2-yl]methanol

生成物 1

HCID 10272552tert-butyl(dimethyl)silyl [(2R)-6-iodo-3,4-dihydro-2H-chromen-2-yl]methyl ether収率 79%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
27 °C

実験手順

A reaction mixture containing [(2R)-6-iodo-3,4-dihydro-2H-chromen-2-yl]methanol (Example 8, 5 g, 17.2 mmol, 1.0 eq), tert-butyldimethylsilyl chloride (20.6 mmol, 1.2 eq), and imidazole (43 mmol, 2.5 eq) in anhydrous DMF (35 mL) was stirred at 27° C. overnight. The resulting mixture was then cooled to room temperature, poured into water, and extracted with diethyl ether. The organic extract was washed with water, brine, dried over anhydrous sodium sulfate, concentrated, and purified by medium pressure column chromatography (Biotage 40S normal phase silica gel column, providing the product in 79% yield; M/z 405 [MH=].

後処理

  1. temperatureThe resulting mixture was then cooled to room temperature
  2. extractionextracted with diethyl ether
  3. extractionThe organic extract
  4. washwas washed with water, brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified by medium pressure column chromatography (Biotage 40S normal phase silica gel column
  8. customproviding the product in 79% yield

出典と根拠

ORDレコード
ord-e9250eeaa6ca4902be2256a984a0b951
出典データセット
uspto-grants-2004_03
特許番号
US06699860B2

関連ノート

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