Dimethylformamide → 3-benzyloxy-N,N-diethyl-2-formyl-4-methoxy-benzamide

HRID 2268868Notizen

Reaktionsgleichung

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:12]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)CCN(C)C.C([Li])(CC)C.CN([CH:40]=[O:41])C>C1COCC1>[CH2:1]([O:8][C:9]1[C:10]([CH:40]=[O:41])=[C:11]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:12]([N:14]([CH2:15][CH3:16])[CH2:17][CH3:18])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

A solution of 3-benzyloxy-N,N-diethyl-4-methoxy-benzamide (39.54 g, 126.2 mmoles), prepared as described in example 55, and tetramethylethylendiamine (16.13 g, 138.8 mmoles) in THF (4,250 ml), cooled to −78° C. under N2, was dropwise added with 1.21M sec-butyl lithium (115.64 ml, 138.8 mmoles). After 2 hours DMF (43 ml, 555 mmoles) was added and the mixture was left at −78° C. for 4 hours, then overnight let the temperature rise. The mixture was washed with a 0.4M pH=7 phosphate buffer, the organic phase was separated and the aqueous one was extracted with ethyl ether. The organic phase was anhydrified and dried to give a solid which was filtered off. The mother liquors were brought to dryness and the crude flash chromatographed (eluent: ethyl acetate/petrolatum 1:1) to give 13.76 g of the title compound (yield: 32%).

Aufarbeitung

customovernight
washThe mixture was washed with a 0.4M pH=7 phosphate buffer
customthe organic phase was separated
extractionthe aqueous one was extracted with ethyl ether
customdried
customto give a solid which
filtrationwas filtered off
customthe crude flash chromatographed (eluent: ethyl acetate/petrolatum 1:1)

Quellen und Nachweise

ORD-Eintrag: ord-40356865a9374d6f9b9a9d34342944fb
Quelldatensatz: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06329370B1

Notizen zur Reaktion

Wird geladen…