Hydrochloric Acid → HCID 21840275, compound

HRID 1739043Notes

Reaction equation

HRID 1739043 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:18][C:19]=2[CH3:20])=[CH:9][CH:8]=1.CN(C)[CH:29]=[O:30].Cl>CCCCCC.O1CCCC1>[CH3:20][C:19]1[O:18][C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:16][C:15]=1/[CH:14]=[CH:13]/[C:10]1[CH:11]=[CH:12][C:7]([CH:29]=[O:30])=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 21840248HCID 21840248, compoundHCID 178418339Butyllithium

Product 1

HCID 21840275HCID 21840275, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of n-butyllithium in hexane (1.6M, 28.7 ml) was added dropwise to a solution of (E)-4-[2-(4-bromophenyl)vinyl]-5-methyl-2-phenyloxazole (13.0 g) in tetrahydrofuran (140 ml) at -70° C. The mixture was stirred at -70° C. for 15 minutes, and then a solution of N,N-dimethylformamide (4.2 g) in tetrahydrofuran (10 ml) was added dropwise at the same temperature. The reaction mixture was stirred at -70° C. for 30 minutes, and then warmed to room temperature. 1N hydrochloric acid (150 ml) was added dropwise, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with ethyl acetate-hexane (1:2, v/v) gave (E)-4-[2-(5-methyl-2-phenyl-4-oxazolyl)vinyl]-benzaldehyde (5.9 g, 54%). The product was recrystallized from ethyl acetate-hexane. Pale brown prisms, mp: 158-159° C.

Workup

  1. stirringThe reaction mixture was stirred at -70° C. for 30 minutes
  2. temperaturewarmed to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe fractions eluted with ethyl acetate-hexane (1:2

Sources & evidence

ORD record
ord-f181b790dbb24cd2bc76dc229d7baed2
Source dataset
uspto-grants-1999_10
Patent number
US05965589

Reaction notes

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