Diisopropylamine → Ethyl 2-formyl-3-methylbutanoate

HRID 237821

반응식

HRID 237821 반응식
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]

참가 물질

7

반응물 4

HCID 7912DiisopropylamineHCID 7945Ethyl isovalerateHCID 8025Ethyl formateHCID 178418339Butyllithium

생성물 2

HCID 13379358Ethyl 2-formyl-3-methylbutanoate수율 181.3%HCID 23449302Methyl acetate hexane

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ad28a19fffd64e2e8c1176bdfc6d3bbf
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642603B2

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