Carbon Dioxide → HCID 21685535, compound

HRID 736861Notes

Reaction equation

HRID 736861 reaction equation
BrC(Br)=C[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].[CH2:19]([Li])[CH2:20]CC.CCCCCC.[C:30](=[O:32])=[O:31].O>O1CCCC1>[Si:11]([O:10][C:5]1[CH:4]=[CH:9][C:8]([CH2:19][CH2:20][C:30]([OH:32])=[O:31])=[CH:7][CH:6]=1)([C:14]([CH3:15])([CH3:16])[CH3:17])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 13170366HCID 13170366, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 21685535HCID 21685535, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1-dibromo-2-(tert-butyldimethylsilyloxyphenyl)ethylene (190.9 mg, 0.487 mmol) prepared in 2) was dissolved in tetrahydrofuran (2.9 ml) in nitrogen atmosphere, and a 1.58 mol/l n-butyllithium/hexane solution (832 μl, 1.31 mmol) was dropwise added at −78° C. After stirring for one hour, crushed dry ice was added to return the solution to 0° C. After stirring for 10 minutes, water was added, and the solution was concentrated under reduced pressure. The residue was diluted with diethyl ether and extracted with water. The obtained aqueous layer was acidified (pH=4) with a saturated potassium hydrogen sulfate aqueous solution and extracted with ethyl acetate. The obtained organic layer was washed with a saturated salt solution, dried over anhydrous sodium sulfate, subjected to filtration and concentrated under reduced pressure to give 3-(4-tert-butyldimethylsilyloxyphenyl)propionic acid (134.6 mg, quant.) as crude crystals.

Workup

  1. additionwas added
  2. customto 0° C
  3. stirringAfter stirring for 10 minutes
  4. concentrationthe solution was concentrated under reduced pressure
  5. additionThe residue was diluted with diethyl ether
  6. extractionextracted with water
  7. extractionextracted with ethyl acetate
  8. washThe obtained organic layer was washed with a saturated salt solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationsubjected to filtration
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1cc1f22203dd46e6b81dae17571be04c
Source dataset
uspto-grants-2009_09
Patent number
US07595415B2

Reaction notes

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