Iodine → 4-(((Tert-butyldimethylsilyl)oxy)methyl)-2-iodothiazole

HRID 1994543

반응식

HRID 1994543 반응식
[Si:1]([O:8][CH2:9][C:10]1[N:11]=[CH:12][S:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li]CCCC.[I:20]I>C1COCC1>[Si:1]([O:8][CH2:9][C:10]1[N:11]=[C:12]([I:20])[S:13][CH:14]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 807IodineHCID 667166624-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]thiazoleHCID 178418339Butyllithium

생성물 1

HCID 534163584-(((Tert-butyldimethylsilyl)oxy)methyl)-2-iodothiazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

To a −78° C. solution of 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1,3-thiazole (106.4 mg, 0.465 mmol) in THF (5 mL) was added dropwise a solution of n-BuLi (465 μL of a 1.6M solution in hexanes, 0.744 mmol). The reaction was stirred at −78° C. for 30 minutes, and then a solution of iodine (295 mg, 1.16 mmol) in THF (5 mL) was added by cannula. The reaction was warmed to room temperature for 15 minutes and then quenched by pouring into aq. NaHSO3 (20 mL). The mixture was extracted with EtOAc (60 mL) and the organic layer was washed with brine, saturated NaHCO3, and brine (20 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography (15% EtOAc/hexanes) afforded 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-iodo-1,3-thiazole. Rf=0.55 (15% EtOAc/hexanes). LCMS=356.0 (M+1)+. 1H NMR (CDCl3, 600 MHz) δ 7.16 (s, 1H), 4.86 (s, 2H), 0.93 (s, 9H), 0.10 (s, 6H).

후처리

  1. temperatureThe reaction was warmed to room temperature for 15 minutes
  2. customquenched
  3. additionby pouring into aq. NaHSO3 (20 mL)
  4. extractionThe mixture was extracted with EtOAc (60 mL)
  5. washthe organic layer was washed with brine, saturated NaHCO3, and brine (20 mL each)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the residue by flash chromatography (15% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-3c2b3196870b4f428203f68185d1f9c8
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652049B2

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