Imidazole → (2R)-1-(benzyloxy)-3-[(triisopropylsilyl)oxy]-2-propanol

HRID 1496907노트

반응식

HRID 1496907 반응식
Cl[Si:2]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[CH:3]([CH3:5])[CH3:4].[CH2:12]([O:19][CH2:20][C@@H:21]([OH:24])[CH2:22][OH:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CN=C1>CN(C=O)C>[CH2:12]([O:19][CH2:20][C@@H:21]([OH:24])[CH2:22][O:23][Si:2]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[CH:3]([CH3:5])[CH3:4])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 69508413-(Benzyloxy)propane-1,2-diol

생성물 1

HCID 66707553(2R)-1-(benzyloxy)-3-[(triisopropylsilyl)oxy]-2-propanol수율 78.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Chloro(triisopropyl)silane (12.2 mL, 0.057 mol) was added dropwise at 20° C. to a stirred solution of diol 78 (9.52 g, 0.052 mol) and imidazole (5.33 g, 0.078 mol) in DMF (150 mL) and stirring was continued for 16 h. Most of the DMF was removed under reduced pressure and the residue was partitioned between EtOAc and water. The organic extract was washed well with water, then brine, and was evaporated to give an oil, which was chromatographed on silica. Elution with petroleum ether gave fore fractions, and then further elution with EtOAc/petroleum ether (1:19) gave (2R)-1-(benzyloxy)-3-[(triisopropylsilyl)oxy]-2-propanol (79) (13.80 g, 78%) as a colourless oil: [α]19 −0.78° (c, 8.93, CHCl3); 1H NMR (CDCl3) δ 7.41-7.27 (m, 5H), 4.55 (s, 2H), 3.90-3.84 (m, 1H), 3.79-3.72 (m, 2H), 3.59-3.51 (m, 2H), 2.52 (d, J=5.1 Hz, 1H), 1.13-1.03 (m, 21H). APCI MS m/z 339 [M+H]+.

후처리

  1. customMost of the DMF was removed under reduced pressure
  2. customthe residue was partitioned between EtOAc and water
  3. extractionThe organic extract
  4. washwas washed well with water
  5. custombrine, and was evaporated
  6. customto give an oil, which
  7. customwas chromatographed on silica
  8. washElution with petroleum ether
  9. customgave fore fractions
  10. washfurther elution with EtOAc/petroleum ether (1:19)

출처 및 근거

ORD 기록
ord-1028d5faab6d4f63a4d0e149d101b6ba
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09198913B2

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