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

HRID 1757501

Reaction equation

C[Si](C)(C)N[Si](C)(C)C.[Li].[CH3:11][O:12][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:32](=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O1CCCC1>[C:33]1([C:32](=[O:39])[C:26]#[C:25][C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([O:18][CH2:17][C:16]3[CH:15]=[CH:14][C:13]([O:12][CH3:11])=[CH:28][CH:27]=3)[CH:20]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=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-(4methoxybenzyloxy)phenylacetylene (0.48 g, 2 mmol) in tetrahydrofuran and stir the brown solution for 45 minutes at 0° C. Add N-methoxy-N-methylbenzamide (0.4 g, 2.4 mmol), remove the cooling bath andstir 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. Recrystallize (hexane, ethyl ether) to yield 0.26 g (lst crop) and 0.15 g (2nd crop) of the title compound; mp 79°-80 C.

Workup

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
customRecrystallize (hexane, ethyl ether)

Sources & evidence

ORD record: ord-48780852258f42e2936b931423a3798e
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05446068

Linked notes

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