HCID 86087083, compound → HCID 68537290, compound

HRID 1992917Notes

Reaction equation

HRID 1992917 reaction equation
CN(OC)[C:3](=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]#[C:11][CH2:12][O:13][CH3:14].[CH2:18]([Mg]Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[CH3:14][O:13][CH2:12][C:11]#[C:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3](=[O:15])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 86087083HCID 86087083, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 68537290HCID 68537290, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Methyl-N-(methyloxy)-2-[3-(methyloxy)-1-propyn-1-yl]benzamide (143) (0.35 g, 1.50 mmol) was treated with benzylmagnesium chloride in THF to give 0.21 g (53%) of the title compound (144) as a light yellow oil. 1H NMR (400 MHz, CDCl3): δ 3.44 (s, 3H), 4.34 (s, 2H), 4.38 (s, 2H), 7.20-7.26 (m, 3H), 7.27-7.38 (m, 3H), 7.38-7.44 (m, 1H), 7.54 (d, J=7.7 Hz, 1H), 7.57 (d, J=7.7 Hz, 1H). LCMS (ESI): m/z 265 (M+H)+.

Sources & evidence

ORD record
ord-f02a5f1c898c4bbeb67e795b56142b59
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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