HCID 86087198, compound → HCID 68539382, compound

HRID 1992896Notes

Reaction equation

HRID 1992896 reaction equation
[C:1]([C:8]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:9]=1[C:10](N(C)OC)=[O:11])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH2:22]([Mg]Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[C:1]([C:8]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:9]=1[C:10](=[O:11])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 86087198HCID 86087198, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 68539382HCID 68539382, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(1-Heptyn-1-yl)-N-methyl-N,4-bis(methyloxy)benzamide (111) (0.58 g, 2.00 mmol) was treated with benzylmagnesium chloride in THF to give 0.57 g (89%) of the title compound (112) as a light yellow oil. 1H NMR (400 MHz, CDCl3): δ 0.89 (t, J=7.2 Hz, 3H), 1.30-1.50 (m, 4H), 1.60-1.70 (m, 2H), 2.45 (t, J=7.2 Hz, 2H), 3.83 (s, 3H), 4.44 (s, 2H), 6.82 (dd, J1=8.8 Hz, J2=2.8 Hz, 1H), 6.97 (d, J=2.7 Hz, 1H), 7.19-7.26 (m, 3H), 7.27-7.32 (m, 2H), 7.65 (d, J=8.8 Hz, 1H). LCMS (ESI): m/z 321 (M+H)+, m/z 319 (M−H)−.

Sources & evidence

ORD record
ord-99e5f815e37b4e29a9d1ccde6195d4fa
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

Loading…