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

HRID 1955694ノート

反応式

HRID 1955694 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  1. distillationfollowed by the vacuum distillation of crude product

出典と根拠

ORDレコード
ord-d9e5479a6ddb42ca8c9810fb47ac4276
出典データセット
uspto-grants-1998_07
特許番号
US05776959

反応ノート

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