2-(1-Hexyn-1-yl)-N-methyl-N-(methyloxy)benzamide → 1-[2-(1-Hexyn-1-yl)phenyl]-2-phenylethanone

HRID 1992939Notes

Reaction equation

HRID 1992939 reaction equation
[C:1]([C:7]1[CH:18]=[CH:17][CH:16]=[CH:15][C:8]=1[C:9](N(C)OC)=[O:10])#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:19]([Mg]Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[C:1]([C:7]1[CH:18]=[CH:17][CH:16]=[CH:15][C:8]=1[C:9](=[O:10])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 107767732-(1-Hexyn-1-yl)-N-methyl-N-(methyloxy)benzamideHCID 178418336HCID 178418336, compound

Product 1

HCID 685346611-[2-(1-Hexyn-1-yl)phenyl]-2-phenylethanoneYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(1-Hexyn-1-yl)-N-methyl-N-(methyloxy)benzamide (158) (1.0 g, 4.08 mmol) was treated with benzylmagnesium chloride in THF at 0° C. to give 0.88 g (78%) of compound 171 as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 0.93 (t, J=7.2 Hz, 3H), 1.40-1.53 (m, 2H), 1.56-1.65 (m, 2H), 2.45 (t, J=7.1 Hz, 2H), 4.43 (s, 2H), 7.20-7.26 (m, 4H), 7.27-7.36 (m, 2H), 7.34-7.39 (m, 1H), 7.45-7.52 (m, 2H). LCMS (ESI): m/z 277 (M+H)+.

Sources & evidence

ORD record
ord-ee5699d7cdae43d2bb36bb2696b822a6
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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