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

HRID 47672

반응식

HRID 47672 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
27 °C

실험 절차

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=].

후처리

  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

출처 및 근거

ORD 기록
ord-e9250eeaa6ca4902be2256a984a0b951
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699860B2

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