Imidazole → Tert-butyl[4-(iodomethyl)phenoxy]dimethylsilane

HRID 2387668노트

반응식

HRID 2387668 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.[Si:27]([O:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39]O)=[CH:37][CH:36]=1)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]>O1CCCC1>[C:30]([Si:27]([O:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][I:25])=[CH:37][CH:36]=1)([CH3:29])[CH3:28])([CH3:33])([CH3:32])[CH3:31]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 10014460(4-((Tert-butyldimethylsilyl)oxy)phenyl)methanol

생성물 1

HCID 21760231Tert-butyl[4-(iodomethyl)phenoxy]dimethylsilane수율 41%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

Triphenyl phosphine (1.32 g, 5.03 mmol), imidazole (370 mg, 5.47 mmol) and iodine (1.16 g, 4.61 mmol) were added to an ice-cooled solution of 4-(tert-butyldimethylsilyloxy)benzyl alcohol [(1 g, 4.19 mmol), Tet. Lett. (2004), 45, 9617] in tetrahydrofuran (50 mL) and the mixture was stirred at 0° C. for 10 minutes and room temperature for 30 minutes. The reaction mixture was then concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was separated, dried over magnesium sulfate and concentrated in vacuo. Purification of the residue by column chromatography on silica gel, eluting with pentane, afforded the title compound in 41% yield, 600 mg.

후처리

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by column chromatography on silica gel
  7. washeluting with pentane

출처 및 근거

ORD 기록
ord-fb03a50cdcef4c07a11a5985894d3d7c
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268881B2

반응 노트

불러오는 중…