Ethyl butyrate → Ethyl 2-formylbutanoate

HRID 2171735

反応式

HRID 2171735 の反応式
C(N[CH:5]([CH3:7])[CH3:6])(C)C.[CH2:8]([Li])[CH2:9][CH2:10]C.[CH2:13]([O:15][C:16](=[O:20])[CH2:17][CH2:18][CH3:19])C.[CH:21]([O:23][CH2:24][CH3:25])=[O:22]>C1COCC1>[C:16]([O:15][CH3:13])(=[O:20])[CH3:17].[CH3:8][CH2:9][CH2:10][CH2:7][CH2:5][CH3:6].[CH2:24]([O:23][C:21](=[O:22])[CH:17]([CH:16]=[O:15])[CH2:18][CH3:19])[CH3:25]

参加物

7

反応物 4

HCID 7762Ethyl butyrateHCID 7912DiisopropylamineHCID 8025Ethyl formateHCID 178418339Butyllithium

生成物 2

HCID 289299Ethyl 2-formylbutanoate収率 194.4%HCID 23449302Methyl acetate hexane

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

A solution of diisopropylamine (10.1 g, 100 mmol) in THF (100 mL) was treated with n-butyllithium (1.6 M in hexane, 63 mL, 100 mmol) at room temperature under N2. The resulting pale yellow solution was cooled to −78° C. A solution of butyric acid ethyl ester (10.4 g, 89.2 mmol) in THF (28 mL) was added. Stirring was continued for a half hour at −78° C., after which ethyl formate (22.0 g, 300 mmol) was added. The reaction mixture was allowed to warm to room temperature and stirred for three hours under N2. The reaction mixture was quenched with acetic acid (˜17 ml), diluted with diethyl ether, washed with water, brine, dried (Na2SO4). Silica gel chromatography (methyl acetate/hexane) provided 12.5 g of the title compound as a mixture of isomers.

後処理

  1. waitwas continued for a half hour at −78° C.
  2. temperatureto warm to room temperature
  3. stirringstirred for three hours under N2
  4. customThe reaction mixture was quenched with acetic acid (˜17 ml)
  5. additiondiluted with diethyl ether
  6. washwashed with water, brine
  7. dry with materialdried (Na2SO4)

出典と根拠

ORDレコード
ord-2702fdc69c6d4d75ba4fa1eac5ea3e56
出典データセット
uspto-grants-2015_06
特許番号
US09051331B2

関連ノート

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