Acetic Acid → HCID 21182319, compound

HRID 1872393Notes

Reaction equation

HRID 1872393 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2C=C[C:11]([CH2:14][CH2:15][CH2:16]CCCC)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:21]([Li])[CH2:22]CC.[C:26]([O:33]CC)(=O)[C:27]([O:29]CC)=O.C(O)(=O)C>O1CCCC1.C(OCC)C.CCCCCC.C(OCC)(=O)C.O>[CH2:21]([C:27](=[O:29])[C:26]([C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:14][CH2:15][CH3:16])=[CH:6][CH:7]=1)=[O:33])[CH3:22]

Participants

10

Reactant 4

HCID 176Acetic AcidHCID 7268Diethyl OxalateHCID 6187104-Bromo-4'-heptylbiphenylHCID 178418339Butyllithium

Product 1

HCID 21182319HCID 21182319, compound

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 4-bromo-4'-n-heptylbiphenyl (2.71 g) in tetrahydrofuran (100 ml) was added dropwise a solution of n-butyllithium in a mixture of diethyl ether and n-hexane (1.6M, 5.1 ml) at -78° C. After stirring at -78° C. for 30 minutes, the resultant mixture was added to a solution of diethyl oxalate (3.4 ml) in tetrahydrofuran (50 ml) at -78° C. The resultant mixture was allowed to warm to 0° C. for about 1 hour, and to the mixture was added acetic acid (0.5 ml). Evaporation gave a residue which was taken up into a mixture of water and ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate. Evaporation gave a residue which was chromatographed on silica gel (200 ml) eluting with a mixture of n-hexane and ethyl acetate (10:0-95:5, V/V) to give 1-Ethyl-2-(4-n-heptylphenyl)ethanedione (2.23 g).

Workup

  1. temperatureto warm to 0° C. for about 1 hour
  2. customEvaporation
  3. customgave a residue which
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation
  8. customgave a residue which
  9. customwas chromatographed on silica gel (200 ml)
  10. washeluting with a mixture of n-hexane and ethyl acetate (10:0-95:5, V/V)

Sources & evidence

ORD record
ord-874f1b7de1f246f0a3216789f75aab2a
Source dataset
uspto-grants-2000_08
Patent number
US06107458

Reaction notes

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