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

HRID 1955694노트

반응식

HRID 1955694 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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 (2.5M, 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).

후처리

  1. distillationfollowed by the vacuum distillation of crude product

출처 및 근거

ORD 기록
ord-d9e5479a6ddb42ca8c9810fb47ac4276
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05776959

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