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

HRID 500610노트

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HRID 500610 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

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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-ab1cbc2d87b54d7aa595fe60cfaa9c58
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772223B2

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