Allyl bromide → Methyl 2-ethyl-2-(1-methylethyl)-4-pentenoate

HRID 1108370Notes

Reaction equation

HRID 1108370 reaction equation
[CH2:1]([CH:3]([CH:8]([CH3:10])[CH3:9])[C:4]([O:6][CH3:7])=[O:5])[CH3:2].[CH2:11](Br)[CH:12]=[CH2:13].C([N-]C(C)C)(C)C.[Li+].CN(P(N(C)C)(N(C)C)=O)C>C1COCC1>[CH2:1]([C:3]([CH:8]([CH3:10])[CH3:9])([CH2:13][CH:12]=[CH2:11])[C:4]([O:6][CH3:7])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 12679HexamethylphosphoramideHCID 2724682Lithium diisopropylamideHCID 12696465Methyl 2-ethyl-3-methylbutyrate

Product 1

HCID 10607559Methyl 2-ethyl-2-(1-methylethyl)-4-pentenoateYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction of methyl 2-ethyl-3-methylbutyrate (23.76 g, 165 mmol), prepared as in Lion C, Dubois J E (1981) supra., with allyl bromide (31.34 g, 259 mmol) in the presence of lithium diisopropylamide (prepared by treating diisopropylamine (25.05 g, 248 mmol) with butyllithium in hexanes (2.5 M, 94.4 mL, 236 mmol)) in THF (330 mL) and HMPA (24.7 mL, 142 mmol), as described above in the preparation of Example 7, followed by the vacuum distillation of crude product afforded the pure olefinic ester (24.85 g, 82%) as a colorless liquid: bp 92-94° C. (20 mmHg).

Workup

  1. distillationfollowed by the vacuum distillation of crude product

Sources & evidence

ORD record
ord-2eacac5ad4454b9ba4977bd957c5d517
Source dataset
uspto-grants-2000_05
Patent number
US06066666

Reaction notes

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