Ethyl Acetoacetate → Ethyl 5-(3-chlorophenyl)-3-oxopentanoate

HRID 326197Notes

Reaction equation

HRID 326197 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21]Cl>C1COCC1>[O:4]=[C:3]([CH2:5][CH2:21][C:20]1[CH:23]=[CH:24][CH:25]=[C:18]([Cl:17])[CH:19]=1)[CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 12103m,alpha-DichlorotolueneHCID 24758Sodium hydrideHCID 178418339Butyllithium

Product 1

HCID 20462750Ethyl 5-(3-chlorophenyl)-3-oxopentanoateYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl acetoacetate (78.6 g, 0.6 mole) was added to a slurry of sodium hydride (20.8 g of 75% dispersion in oil, 0.65 mole) in dry THF at 0° C. under nitrogen followed by addition of n-butyl lithium (390 ml, 1.6 M in hexane, 0.63 mole) by the method given in Description 1(a). 3-Chlorobenzyl chloride (100 g, 0.62 mole) was added and after work-up and purification by vacuum distillation the required product was obtained as a very pale yellowish green oil (97.3 g, 64%), δ(CDCl3) 7.3-6.9 (4H, m), 4.18 (2H, q, J=7 Hz), 3.42 (2H, s), 2.88 (4H, s), and 1.27 (3H, t, J=7 Hz).

Workup

  1. customafter work-up and purification
  2. distillationby vacuum distillation the required product

Sources & evidence

ORD record
ord-c0774fe6fb9a402ab0aacbe1f21c9e38
Source dataset
uspto-grants-1984_04
Patent number
US04444981

Reaction notes

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