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

HRID 1994543ノート

反応式

HRID 1994543 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3c2b3196870b4f428203f68185d1f9c8
出典データセット
uspto-grants-2010_01
特許番号
US07652049B2

反応ノート

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