Benzyl 3-hydroxybutanoate → Benzyl crotonate, (E)-

HRID 1450729Notes

Reaction equation

HRID 1450729 reaction equation
O[CH:2]([CH3:14])[CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]>CC#N.Cl[Cu]>[C:4]([O:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)(=[O:5])/[CH:3]=[CH:2]/[CH3:14]

Participants

4

Reactant 1

HCID 562226Benzyl 3-hydroxybutanoate

Product 1

HCID 5356259Benzyl crotonate, (E)-Yield 83%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Benzyl 3-hydroxyl-butanoate (Sakaki et al., Chem. Pharm. Bull., 37, p. 2952 (1989)) (0.46 g, 2.4 mmol), CuCl (11 mg, 5 mol %), and 1 (0.7 g, 110 mol %) were combined in 20 mL of dry CH3CN and heated to 60° C. for 16 h. The reaction mixture was cooled and evaporated, followed by isolation according to the general procedure to give benzyl crotonate (0.346 g, 83%) as a mobile oil: IR 3060, 3030, 1720; 1H NMR δ 7.40-7.20 (m, 5H), 7.00 (dq, 1H, J=15.5, 6.9), 5.86 (dq, 1H, J=16.0, 1.6), 5.18 (s, 2H), 1.83 (dd, 3H, J=1.7, 6.9).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated

Sources & evidence

ORD record
ord-2145b85e59334c1ca0a7dbfcded05095
Source dataset
uspto-grants-1997_02
Patent number
US05602264

Reaction notes

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