Hydrochloric Acid → 3-cyclopentyloxy-N,N-diethyl-2-formyl-4-methoxy-benzamide

HRID 1250852Notes

Reaction equation

C([Li])(CC)C.CN(C)[CH:8]=[O:9].[CH:11]1([O:16][C:17]2[CH:18]=[C:19]([CH:27]=[CH:28][C:29]=2[O:30][CH3:31])[C:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:21])[CH2:15][CH2:14][CH2:13][CH2:12]1.NCCCCN.P([O-])([O-])([O-])=O.Cl>O1CCCC1.C(OCC)(=O)C>[CH:11]1([O:16][C:17]2[C:18]([CH:8]=[O:9])=[C:19]([CH:27]=[CH:28][C:29]=2[O:30][CH3:31])[C:20]([N:22]([CH2:23][CH3:24])[CH2:25][CH3:26])=[O:21])[CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

Conditions

Temperature: -75 °C

Procedure

At −75° C. under stirring, sec-butyl-lithium (195.76 ml, 0.231 moles) and, after 1 hour, at the same temperature, dimethylformamide (53.66 ml, 0.693 moles) were added dropwise to a solution of 3-cyclopentyloxy-N,N-diethyl-4-methoxy-benzamide (61.2 g, 0.21 moles), obtained as described in example 3, and of tetramethylendiamine (34.86 ml, 0.231 moles) in anhydrous tetrahydrofuran (480 ml). After further half an hour at −75° C., the reaction mixture was poured into a pH=7 phosphate buffer, ethyl acetate and concentrated HCl. The extraction was repeated further twice with fresh ethyl acetate, then the extract was washed with 5% potassium bisulphate, then with water, then dried on sodium sulphate and evaporated to dryness. The residue was cromatographed on silica gel (eluent petrolatum/ethyl acetate 1:1) to give 23.3 g of the title compound (yield: 35%).

Workup

customobtained
waitAfter further half an hour at −75° C.
extractionThe extraction
washthe extract was washed with 5% potassium bisulphate
dry with materialwith water, then dried on sodium sulphate
customevaporated to dryness

Sources & evidence

ORD record: ord-c9f6e476611944c1a284092dd39a0706
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06340684B1

Reaction notes

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