2-(1-Hexyn-1-yl)-N-methyl-N-(methyloxy)benzamide → 2-(4-Fluorophenyl)-1-[2-(1-hexyn-1-yl)phenyl]ethanone

HRID 1992935Notes

Reaction equation

HRID 1992935 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].[F:19][C:20]1[CH:28]=[CH:27][C:23]([CH2:24][Mg]Cl)=[CH:22][CH:21]=1>C1COCC1>[F:19][C:20]1[CH:28]=[CH:27][C:23]([CH2:24][C:9]([C:8]2[CH:15]=[CH:16][CH:17]=[CH:18][C:7]=2[C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH3:6])=[O:10])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 107767732-(1-Hexyn-1-yl)-N-methyl-N-(methyloxy)benzamideHCID 178505759HCID 178505759, compound

Product 1

HCID 685385242-(4-Fluorophenyl)-1-[2-(1-hexyn-1-yl)phenyl]ethanoneYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(1-Hexyn-1-yl)-N-methyl-N-(methyloxy)benzamide (158) (0.50 g, 2.04 mmol) was treated with 4-fluorobenzylmagnesium chloride in THF at room temperature to give 0.37 g (61%) of compound (165) 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), 4.40 (s, 2H), 6.99 (t, J=8.6 Hz, 2H), 7.16-7.22 (m, 2H), 7.26-7.32 (m, 1H), 7.35-7.41 (m, 1H), 7.45-7.52 (m, 2H).

Sources & evidence

ORD record
ord-a7af97f6837643d583edc3a4b8128a78
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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