Imidazole → Tri-isopropyl-(2-trifluoromethyl-furan-3-ylmethoxy)-silane

HRID 490364Notes

Reaction equation

HRID 490364 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[O:4][CH:5]=[CH:6][C:7]=1[CH2:8][OH:9].CC1OC=CC=1CCO.Cl[Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24].N1C=CN=C1>ClCCl.O>[CH:23]([Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[O:9][CH2:8][C:7]1[CH:6]=[CH:5][O:4][C:3]=1[C:2]([F:1])([F:10])[F:11])([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 795Imidazole2×HCID 139400Triisopropylsilyl chloride2×HCID 17953606(2-Trifluoromethyl-furan-3-yl)-methanolHCID 184446362-(2-Methylfuran-3-yl)ethan-1-ol

Product 1

HCID 18444682Tri-isopropyl-(2-trifluoromethyl-furan-3-ylmethoxy)-silane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the (2-trifluoromethyl-furan-3-yl)-methanol from (i) in dry dichloromethane (180 ml) was treated with chloro-tri-isopropyl-silane (2.6 g, 13.4 mmoles) and imidazole (1.45 g, 21.3 mmoles) and the mixture was stirred overnight at room temperature. Further aliquots of chloro-tri-isopropyl-silane (0.9 g, 4.64 mmoles) and imidazole (0.5 g, 7.34 mmoles) were added and the mixture was stirred for 3 h. The reaction mixture was diluted with water, the organic phase separated and washed sequentially with 0.1M aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate, water and brine. After drying, evaporation of the solvents afforded a colourless oil. The oil was distilled under reduced pressure (0.05 torr) in a Kugelruhr apparatus collecting the fraction boiling at an oven temperature of 125±20° C. to afford compound 88 as a colourless oil.

Workup

  1. stirringthe mixture was stirred for 3 h
  2. customthe organic phase separated
  3. washwashed sequentially with 0.1M aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate, water and brine
  4. customAfter drying
  5. customevaporation of the solvents
  6. customafforded a colourless oil
  7. distillationThe oil was distilled under reduced pressure (0.05 torr) in a Kugelruhr apparatus
  8. customcollecting the fraction
  9. customboiling at an oven

Sources & evidence

ORD record
ord-07ad163b6cf849129ecc6c24c453d60a
Source dataset
uspto-grants-2009_05
Patent number
US07528157B2

Reaction notes

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