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

HRID 1250858Notes

Reaction equation

C([Li])(CC)C.C1CCCCC1.CCCCCC.[CH2:18]([O:25][C:26]1[CH:27]=[C:28]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[C:29]([N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])=[O:30])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CN(C)CCN(C)C.CN([CH:52]=[O:53])C>C1COCC1>[CH2:18]([O:25][C:26]1[C:27]([CH:52]=[O:53])=[C:28]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[C:29]([N:31]([CH2:32][CH3:33])[CH2:34][CH3:35])=[O:30])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: -70 °C

Procedure

1.3 M sec-butyl-lithium in cyclohexane/hexane (54 ml, 0.07 moles) was dropped into a solution under nitrogen of 3-benzyloxy-N,N-diethyl-4-methoxy-benzamide (20 g, 0.064 moles), obtained as described in example 31, tetramethylethylendiamine (10.56 ml, 0.07 moles) in THF (2.25 1) under stirring in a dry ice bath at −70° C. After 2 hours at constant temperature, DMF (21.75 ml, 0.28 moles) was added. The temperature was kept constant for 4 hours then left overnight. The mixture was poured into a NaH2PO4/Na2HPO4 buffer solution (1 l) at pH=7, the phases were separated, the organic one was washed with water (1 l), dried and brought to dryness. The crude was chromatographed (eluent: benzene:ethyl acetate 1:1) to give 6 g of the title compound (yield: 27.4%).

Workup

customobtained
waitthen left overnight
customthe phases were separated
washthe organic one was washed with water (1 l)
customdried
customThe crude was chromatographed (eluent: benzene:ethyl acetate 1:1)

Sources & evidence

ORD record: ord-a5dd7ad6e67d4172a0a86f09c529c901
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06340684B1

Reaction notes

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