Acetic Anhydride → HCID 53989203, compound

HRID 440962Notes

Reaction equation

HRID 440962 reaction equation
[H-].[Na+].O[CH:4]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]=1)[CH2:5][C:6]#[N:7].[H][H].C(OC(=O)C)(=O)C>O1CCCC1.O>[C:14]1([C:10]2[CH:9]=[C:8]([CH:4]=[CH:5][C:6]#[N:7])[CH:13]=[CH:12][CH:11]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 19955513HCID 19955513, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53989203HCID 53989203, compoundYield 40.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere a mixture of 1.9 grams (0.048 mole) of sodium hydride (60% in mineral oil) in 50 mL of tetrahydrofuran was stirred, and a solution of 10.7 grams (0.048 mole) of 3-hydroxy-3-(3-phenylphenyl)propanenitrile in 100 mL of tetrahydrofuran was added dropwise. Upon completion of addition, the reaction mixture was stirred until the evolution of hydrogen gas ceased. After this time the reaction mixture was cooled in an ice-bath, and 4.6 mL (0.048 mole) of acetic anhydride was added dropwise. Upon completion of addition, the reaction was allowed to warm to ambient temperature where it was stirred for about 18 hours. The reaction mixture was poured into 300 mL of water, and the mixture was extracted with 200 mL of diethyl ether. The extract was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was subjected to column chromatography on silica gel using methylene chloride as an eluant. The appropriate fractions were combined and concentrated under reduced pressure, yielding 4.0 grams of 3-(3-phenylphenyl)-2-propenenitrile. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. temperatureAfter this time the reaction mixture was cooled in an ice-bath
  3. additionUpon completion of addition
  4. stirringwas stirred for about 18 hours
  5. extractionthe mixture was extracted with 200 mL of diethyl ether
  6. dry with materialThe extract was dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-61e26c500afc45009b3232c73c91ec8d
Source dataset
uspto-grants-1996_05
Patent number
US05521192

Reaction notes

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