N-Methyl-N,4-bis(methyloxy)-2-(4-methyl-1-pentyn-1-yl)benzamide → 1-[4-(Methyloxy)-2-(4-methyl-1-pentyn-1-yl)phenyl]-2-phenylethanone

HRID 1992889Notes

Reaction equation

HRID 1992889 reaction equation
CN(OC)[C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[C:12]#[C:13][CH2:14][CH:15]([CH3:17])[CH3:16].[CH2:21]([Mg]Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3](=[O:18])[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:5]([C:12]#[C:13][CH2:14][CH:15]([CH3:16])[CH3:17])[CH:6]=1

Participants

4

Reactant 2

HCID 86087188N-Methyl-N,4-bis(methyloxy)-2-(4-methyl-1-pentyn-1-yl)benzamideHCID 178418336HCID 178418336, compound

Product 1

HCID 685346851-[4-(Methyloxy)-2-(4-methyl-1-pentyn-1-yl)phenyl]-2-phenylethanoneYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Methyl-N,4-bis(methyloxy)-2-(4-methyl-1-pentyn-1-yl)benzamide (103) (0.72 g, 2.62 mmol) was treated with benzylmagnesium chloride in THF to give 0.73 g (91%) of the title compound (104) as a light yellow oil. 1H NMR (400 MHz, CDCl3): δ 1.04 (d, J=6.6 Hz, 6H), 1.85-2.00 (m, 1H), 2.35 (d, J=6.6 Hz, 2H), 3.83 (s, 3H), 4.44 (s, 2H), 6.82 (dd, J1=8.8 Hz, J2=2.5 Hz, 1H), 6.98 (d, J=2.5 Hz, 1H), 7.19-7.25 (m, 3H), 7.26-7.32 (m, 2H), 7.65 (d, J=8.8 Hz, 1H). LCMS (APCI): m/z 307 (M+H)+.

Sources & evidence

ORD record
ord-0e195714489d4bfcbacbcce5c7407133
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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