Carbon Dioxide → HCID 58306858, compound

HRID 1909881Notes

Reaction equation

HRID 1909881 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH:12](O[Si](C(C)(C)C)(C)C)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:8]=[CH:7]2.C1COCC1.CCCCCC.C([Li])CCC.[C:43](=[O:45])=[O:44]>C(OCC)C>[C:13]1(/[CH:12]=[CH:11]/[N:9]2[C:10]3[C:6](=[CH:5][CH:4]=[CH:3][C:2]=3[C:43]([OH:45])=[O:44])[CH:7]=[CH:8]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 8028TetrahydrofuranHCID 58306784HCID 58306784, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 58306858HCID 58306858, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To 7-bromo-1-(2-{[tert-butyl(dimethyl)silyl]oxy}-2-phenylethyl)-1H-indole (0.91 g) was added dehydrated THF (30 mL), and an n-butyl lithium hexane solution (1.6 M, 5.2 mL) was added thereto at −78° C. while replacing with argon. The mixture was warmed from −78° C. to −5° C., followed by stirring for 30 minutes. The reaction mixture was again cooled to −78° C., and dry ice was added thereto, followed by stirring to room temperature. To the mixture was added diethyl ether, followed by washing with a 1 M aqueous sodium hydroxide solution. The obtained aqueous layer was adjusted to pH 3 with a 10% aqueous citric acid solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to obtain 1-[(E)-2-phenyl vinyl]-1H-indole-7-carboxylic acid (0.34 g).

Workup

  1. customat −78° C.
  2. temperatureThe mixture was warmed from −78° C. to −5° C.
  3. stirringby stirring to room temperature
  4. washby washing with a 1 M aqueous sodium hydroxide solution
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-73b2a9712db941c9a7654066ca6181bb
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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