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

HRID 2300051Notes

Reaction equation

C([Li])(CC)C.[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[C:17]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[O:18])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CN(C)CCN(C)C.CN([CH:40]=[O:41])C>C1COCC1>[CH2:6]([O:13][C:14]1[C:15]([CH:40]=[O:41])=[C:16]([CH:24]=[CH:25][C:26]=1[O:27][CH3:28])[C:17]([N:19]([CH2:20][CH3:21])[CH2:22][CH3:23])=[O:18])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: -70 °C

Procedure

1.3 M sec-butyl-lithium in cyclohexanelhexane (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 l) 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-a55c02f4fca244c098be8b18cd0755bb
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498160B2

Reaction notes

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