Ethyl butyrate → Ethyl 2-formylbutanoate

HRID 2171735

Reaction equation

HRID 2171735 reaction equation
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]

Participants

7

Reactant 4

HCID 7762Ethyl butyrateHCID 7912DiisopropylamineHCID 8025Ethyl formateHCID 178418339Butyllithium

Product 2

HCID 289299Ethyl 2-formylbutanoateYield 194.4%HCID 23449302Methyl acetate hexane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-2702fdc69c6d4d75ba4fa1eac5ea3e56
Source dataset
uspto-grants-2015_06
Patent number
US09051331B2

Linked notes

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