Carbon Dioxide → HCID 90370043, compound

HRID 2175999Notes

Reaction equation

HRID 2175999 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[C:33](=[O:35])=[O:34].Cl>C(OCC)(=O)C.O.C1COCC1>[Si:11]([O:10][CH2:9][CH2:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[C:33]([OH:35])=[O:34])([C:24]([CH3:25])([CH3:26])[CH3:27])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 69853166HCID 69853166, compoundHCID 178418339Butyllithium

Product 1

HCID 90370043HCID 90370043, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

To a mixture of 3.27 g of [2-(3-bromophenyl)ethoxy](tert-butyl)diphenylsilane and 50 mL of THF was slowly added 5.5 mL of butyllithium (1.62 M hexane solution) at −78° C., followed by stirring for 30 minutes at −78° C. In addition, carbon dioxide was blown into the reaction mixture at −78° C., and the temperature thereof was slowly increased to room temperature, followed by stirring for 1 hour at room temperature. Water was added to the reaction mixture, and the mixture was neutralized with 9.0 ml of 1.0 M hydrochloric acid. Ethyl acetate was added thereto to separate the organic layer, the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:6), thereby obtaining 1.45 g of 3-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)benzoic acid.

Workup

  1. customat −78° C.
  2. customwas blown into the reaction mixture at −78° C.
  3. temperaturethe temperature thereof was slowly increased to room temperature
  4. stirringby stirring for 1 hour at room temperature
  5. customto separate the organic layer
  6. washthe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:6)

Sources & evidence

ORD record
ord-7322b575294a408a841ec87746a7d40b
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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