Propanal → 6-(1-hydroxyethyl)-2-methoxy-N,N-diethyl-benzamide

HRID 22171Notes

Reaction equation

C([Li])(CC)C.[CH3:6][O:7][C:8]1[CH:20]=[CH:19][CH:18]=[CH:17][C:9]=1[C:10]([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[O:11].CN(C)CCN(C)C.[CH:29](=[O:32])[CH2:30]C>O1CCCC1.C(OCC)C>[OH:32][CH:29]([C:17]1[C:9]([C:10]([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[O:11])=[C:8]([O:7][CH3:6])[CH:20]=[CH:19][CH:18]=1)[CH3:30]

Participants

Conditions

Temperature: -78 °C

Procedure

13.7 ml of sec-butyllithium (1.4M in cyclohexane/isopentane) are added dropwise to a solution of 5.2 g of 2-methoxy-N,N-diethyl-benzamide and 2.91 g of tetramethylethylenediamine in 50 ml of absolute tetrahydrofuran in such a manner that the temperature does not exceed -68° C. When the addition is complete, the reaction mixture is stirred at -78° C. for a further hour and then 2.5 ml of propionaldehyde are added. The reaction mixture is allowed to warm slowly to room temperature, is subsequently stirred for one hour and is diluted with 300 ml of diethyl ether. The organic phase is washed with 2N hydrochloric acid and then with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated by evaporation to yield 6-(1-hydroxyethyl)-2-methoxy-N,N-diethyl-benzamide in the form of a crude product.

Workup

customdoes not exceed -68° C
additionWhen the addition
temperatureto warm slowly to room temperature
stirringis subsequently stirred for one hour
washThe organic phase is washed with 2N hydrochloric acid
dry with materialwith saturated sodium chloride solution, dried over anhydrous magnesium sulfate
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-ce23fcfb611f442d921e046fb423ba08
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05428002

Reaction notes

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