Water → 4-Hydroxy-2-butynyl 4-Cyano-3,4-diphenylbutyrate

HRID 851280

Reaction equation

HRID 851280 reaction equation
[C:1]([CH:3]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:5][C:6](Cl)=[O:7])#[N:2].[CH2:21]([OH:26])[C:22]#[C:23][CH2:24][OH:25].N1C=CC=CC=1.O>C1C=CC=CC=1.C1COCC1>[C:1]([CH:3]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:5][C:6]([O:25][CH2:24][C:23]#[C:22][CH2:21][OH:26])=[O:7])#[N:2]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 80662-Butyne-1,4-diolHCID 128348424-Cyano-3,4-diphenylbutyryl chloride

Product 1

HCID 128348444-Hydroxy-2-butynyl 4-Cyano-3,4-diphenylbutyrate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10.7 g (0.038 mol) of 4-cyano-3,4-diphenylbutyryl chloride in 30 ml of benzene was added over a 45 minute period to a stirred solution of 6.5 g (0.076 mol) of 2-butyn-1,4-diol and 3.4 ml of pyridine in 100 ml of THF at 0°. The reaction mixture was stirred for 24 hours at room temperature in a flask equipped with a Drierite tube. The solution was poured into 50 ml of water and the layers were separated. Two 60-ml ether extractions of the aqueous layer were combined with the THF layer, were washed twice with 100 ml of H2O, with 100 ml saturated aqueous sodium bicarbonate, and with 100 ml saturated aqueous sodium chloride and were stirred over MgSO4. The filtered solution was stripped and purified by column chromatography on silica gel (hexanes/methylene chloride) to give two fractions weighing 12.6 g (47%) having different isomer ratios as determined from the nmr spectra. The infrared and nmr spectra are in accord with the assigned structure.

Workup

  1. customequipped with a Drierite tube
  2. customthe layers were separated
  3. extractionTwo 60-ml ether extractions of the aqueous layer
  4. washwere washed twice with 100 ml of H2O, with 100 ml saturated aqueous sodium bicarbonate
  5. stirringwith 100 ml saturated aqueous sodium chloride and were stirred over MgSO4
  6. custompurified by column chromatography on silica gel (hexanes/methylene chloride)
  7. customto give two fractions

Sources & evidence

ORD record
ord-8fbe58e249754623aa84a0c45bf15552
Source dataset
uspto-grants-1983_05
Patent number
US04383848

Linked notes

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