Hydrochloric Acid → HCID 11208635, compound

HRID 1386613Notes

Reaction equation

HRID 1386613 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[C:28](=[O:30])[CH3:29].Cl>O1CCCC1.CCCCCC.C(OCC)C.C(OCC)(=O)C.O>[C:28]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1)(=[O:30])[CH3:29]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 31374DimethylacetamideHCID 6187104-Bromo-4'-heptylbiphenylHCID 178418339Butyllithium

Product 1

HCID 11208635HCID 11208635, compound

Reagents, catalysts & solvents 5

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

Conditions

Temperature
-60 °C

Procedure

To a solution of 4-bromo-4′-n-heptylbiphenyl (5.1 g) in tetrahydrofuran (60 ml) was added a solution of #n-butyllithium in a mixture of n-hexane and diethyl ether (1.6M, 9.7 ml) at −60° C. After stirring at −60° C. for 30 minutes, to the mixture was added N,N-dimethylacetamide (4.3 ml) and the reaction mixture was allowed to warm to 0° C. The reaction mixture was taken up into a mixture of cold water and ethyl acetate, and the pH was adjusted to around 1 with 1N hydrochloric acid. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (150 ml) eluting with a mixture of n-hexane and ethyl acetate (20:1, V/V) to give 4-Acetyl-4′-n-heptylbiphenyl (1.60 g).

Workup

  1. temperatureto warm to 0° C
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (150 ml)
  7. washeluting with a mixture of n-hexane and ethyl acetate (20:1, V/V)

Sources & evidence

ORD record
ord-a65ec7d1417f4ad79f30cd659d43a306
Source dataset
uspto-grants-2001_07
Patent number
US06265536B1

Reaction notes

Loading…