Thiazole → 1-{[Tert-butyl(dimethyl)silyl]oxy}-2-(1,3-thiazol-2-yl)propan-2-ol

HRID 1039939노트

반응식

HRID 1039939 반응식
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Si:6]([O:13][CH2:14][C:15](=[O:17])[CH3:16])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]>C1COCC1>[Si:6]([O:13][CH2:14][C:15]([C:2]1[S:1][CH:5]=[CH:4][N:3]=1)([OH:17])[CH3:16])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

참가 물질

4

반응물 2

HCID 9256ThiazoleHCID 41249691-(tert-Butyldimethylsilyloxy)-2-propanone

생성물 1

HCID 674295761-{[Tert-butyl(dimethyl)silyl]oxy}-2-(1,3-thiazol-2-yl)propan-2-ol수율 40%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

Isopropylmagnesium chloride-lithium chloride complex (2.98 ml, 3.88 mmol) was dissolved in THF (4 mL). Thiazole (0.252 ml, 3.52 mmol) in THF (2 mL) was added slowly. After 1 h, 1-(tert-butyldimethylsilyloxy)-2-propanone (0.816 ml, 423 mmol) in THF (2 mL) was added and the reaction was stirred for 3 h at room temperature. The reaction was quenched with saturated ammonium chloride and extracted with EtOAc (3×). The combined organics were dried over Na2SO4, filtered and concentrated in vacuo. Purification via silica gel column chromatography (5%-10% EtOAc:hexanes) afforded 1-{[tert-butyl(dimethyl)silyl]oxy}-2-(1,3-thiazol-2-yl)propan-2-ol (383 mg, 40%) as a yellow oil. MS ESI: [M+H]+ m/z 274.

후처리

  1. customThe reaction was quenched with saturated ammonium chloride
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification via silica gel column chromatography (5%-10% EtOAc:hexanes)

출처 및 근거

ORD 기록
ord-b52ce5dd80c5488481844cb3b9da0a3f
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551984B2

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