Diisopropylamine → Ethyl 2-formyl-3-methylbutanoate

HRID 237821

反応式

HRID 237821 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:21])[CH2:17][CH:18]([CH3:20])[CH3:19])C.[CH:22]([O:24][CH2:25][CH3:26])=[O:23]>C1COCC1>[C:16]([O:15][CH3:13])(=[O:21])[CH3:17].[CH3:8][CH2:9][CH2:10][CH2:7][CH2:5][CH3:6].[CH2:25]([O:24][C:22](=[O:23])[CH:17]([CH:16]=[O:15])[CH:18]([CH3:20])[CH3:19])[CH3:26]

参加物

7

反応物 4

HCID 7912DiisopropylamineHCID 7945Ethyl isovalerateHCID 8025Ethyl formateHCID 178418339Butyllithium

生成物 2

HCID 13379358Ethyl 2-formyl-3-methylbutanoate収率 181.3%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 (2.53 g, 25 mmol) in THF (25 mL) was treated with n-butyllithium (1.6M in hexane, 16 mL, 25.6 mmol) at room temperature under N2. The resulting pale yellow solution was cooled to −78° C. A solution of 3-methyl-butyric acid ethyl ester (2.91 g, 22.31 mmol) in THF (7 mL) was added. Stirring was continued for a half hour at −78° C., after which ethyl formate (5.5 g, 75 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 (4.5 ml), diluted with diethyl ether, washed with water, brine, and dried (Na2SO4). Silica gel chromatography (methyl acetate/hexane) provided 3.2 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 (4.5 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-ad28a19fffd64e2e8c1176bdfc6d3bbf
出典データセット
uspto-grants-2014_02
特許番号
US08642603B2

関連ノート

読み込み中…