Carbon Dioxide → HCID 19010178, compound

HRID 466497Notes

Reaction equation

HRID 466497 reaction equation
C([Li])CCC.[CH2:6]([O:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=1)[CH2:7][CH2:8][CH3:9].[C:19](=[O:21])=[O:20].CCOCC>C1COCC1>[CH2:6]([O:10][C:11]1[CH:12]=[C:13]([F:18])[C:14]([C:19]([OH:21])=[O:20])=[C:15]([F:17])[CH:16]=1)[CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 3283Diethyl EtherHCID 190101831-Butoxy-3,5-difluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 19010178HCID 19010178, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of n-butyllithium (10.5M in hexane; 3.60 ml, 0.038 mol) was added dropwise to a stirred, cooled (-78° C.) solution of compound 16 (7.00 g, 0.038 mol) in dry THF (35 ml) under dry nitrogen. The stirred mixture was maintained under these conditions for 2.5 h and then poured onto a slurry of solid carbon dioxide and dry ether. The product was extracted into 10% sodium hydroxide which was then acidified with 36% hydrochloric acid. The product was filtered off and dried (CaCl2) in vacuo to give a colourless solid.

Workup

  1. temperatureThe stirred mixture was maintained under these conditions for 2.5 h
  2. extractionThe product was extracted into 10% sodium hydroxide which
  3. filtrationThe product was filtered off
  4. dry with materialdried (CaCl2) in vacuo
  5. customto give a colourless solid

Sources & evidence

ORD record
ord-29507184b0814406ac19cfb9bafe6920
Source dataset
uspto-grants-1992_10
Patent number
US05156763

Reaction notes

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