Benzyl Bromide → 4-Pentenoic acid, phenylmethyl ester

HRID 1912918Notes

Reaction equation

HRID 1912918 reaction equation
C([O-])([O-])=O.[K+].[K+].[C:7]([OH:13])(=[O:12])[CH2:8][CH2:9][CH:10]=[CH2:11].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C.O>[C:7]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:12])[CH2:8][CH2:9][CH:10]=[CH2:11]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 611384-Pentenoic acid

Product 1

HCID 100520354-Pentenoic acid, phenylmethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of K2CO3 (4.17 g, 30.2 mmol) and pent-4-enoic acid (3.01 g, 29.2 mmol) in DMF (25 mL) was stirred at room temperature for 5 minutes. Benzyl bromide (3.55 mL, 29.3 mmol) was added from a syringe over 3 minutes, and the resulting white suspension was stirred at room temperature for 23 hours, then diluted with water (150 mL) and extracted with EtOAc (3×50 mL). The combined extract was washed with saturated brine (30 mL) and concentrated under vacuum to leave the title compound. 1H NMR (300 MHz, CD3OD) δ ppm 2.30-2.41 (m, 2H) 2.42-2.50 (m, 2H) 4.96 (dddd, J=10.2, 1.7, 1.4, 1.0 Hz, 1H) 5.03 (dq, J=17.3, 1.6 Hz, 1H) 5.11 (s, 2H) 5.82 (tdd, J=17.0, 10.4, 6.3 Hz, 1H) 7.25-7.38 (m, 5H).

Workup

  1. stirringthe resulting white suspension was stirred at room temperature for 23 hours
  2. extractionextracted with EtOAc (3×50 mL)
  3. extractionThe combined extract
  4. washwas washed with saturated brine (30 mL)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c602e7df73d64f2dbb3d6742c75144ac
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

Loading…