N-Methoxy-N-methylbenzamide → 1-Phenyl-3-[3-(4-(dimethylamino)benzyloxy)phenyl]-2-propyne-1-one

HRID 6498

Reaction equation

C[Si](C)(C)N[Si](C)(C)C.[Li].[CH3:11][N:12]([CH3:29])[C:13]1[CH:28]=[CH:27][C:16]([CH2:17][O:18][C:19]2[CH:20]=[C:21]([C:25]#[CH:26])[CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:14]=1.CON(C)[C:33](=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O1CCCC1>[C:34]1([C:33](=[O:40])[C:26]#[C:25][C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([O:18][CH2:17][C:16]3[CH:27]=[CH:28][C:13]([N:12]([CH3:11])[CH3:29])=[CH:14][CH:15]=3)[CH:20]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Place lithium hexamethyldisilazane (2 mL of a 1M solution in tetrahydrofuran, 2 mmol) and tetrahydrofuran (8 mL) under an argon atmosphere and cool to 0° C. Add a solution of 3-(4-(dimethylamino)benzyloxy)phenylacetylene (0.51 g, 2 mmol) in tetrahydrofuran and stir the solution for 45 minutes at 0° C. Add N-methoxy-N-methylbenzamide (0.4 g, 2.4 mmol), remove the cooling bath and stir at room temperature for 1 hour. Partition the mixture between ethyl ether and water, separate the organic phase and dry (MgSO4). Filter and evaporate the solvent in vacuo to yield an oil. Filter through silica gel and elute with 10% ethyl acetate/hexane to yield a crude solid. Purify by silica gel chromatography to give the title compound.

Workup

stirringstir at room temperature for 1 hour
customPartition the mixture between ethyl ether and water
customseparate the organic phase
dry with materialdry (MgSO4)
filtrationFilter
customevaporate the solvent in vacuo
customto yield an oil
filtrationFilter through silica gel
washelute with 10% ethyl acetate/hexane
customto yield a crude solid
customPurify by silica gel chromatography

Sources & evidence

ORD record: ord-1dcbf41e8a1e4ec0990437ca83de30a4
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05248825

Linked notes

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