Imidazole → Tert-butyl(2-fluoro-3-iodopropoxy)diphenylsilane

HRID 1847021Notes

Reaction equation

HRID 1847021 reaction equation
[Si:1]([O:18][CH2:19][CH:20]([F:23])[CH2:21]O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:24]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[C:14]([Si:1]([O:18][CH2:19][CH:20]([F:23])[CH2:21][I:24])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:16])([CH3:17])[CH3:15]

Participants

7

Reactant 5

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 24477Sodium ThiosulfateHCID 579797963-((Tert-butyldiphenylsilyl)oxy)-2-fluoropropan-1-OL

Product 1

HCID 86724949Tert-butyl(2-fluoro-3-iodopropoxy)diphenylsilaneYield 58.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-{[Tert-Butyl(diphenyl)silyl]oxy}-2-fluoropropan-1-ol(2.03 g, 6.12 mmol) was dissolved in dichloromethane (20 ml). Iodine (4.66 g, 18.36 mmol), triphenyl phosphine (4.82 g, 18.36 mmol) and imidazole (1.25 g, 18.36 mmol) were added to the solution under cooling on ice and the mixture was stirred at room temperature for 23 hours. A saturated sodium thiosulfate aqueous solution was added to the reaction solution under cooling on ice and stirred for a while, the solution was extracted with dichloromethane and the extract was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 1.58 g (58%) of the title compound in the form of a yellowish solid.

Workup

  1. temperatureunder cooling on ice
  2. temperatureunder cooling on ice
  3. stirringstirred for a while
  4. extractionthe solution was extracted with dichloromethane
  5. dry with materialthe extract was dried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e0a200a100564a9e8b9c815b1c2f1500
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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