HCID 86087094, compound → HCID 68534812, compound

HRID 1992923Notes

Reaction equation

HRID 1992923 reaction equation
[CH:1]1([C:4]#[C:5][C:6]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:7]=2[C:8](N(C)OC)=[O:9])[CH2:3][CH2:2]1.[CH2:20]([Mg]Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[CH:1]1([C:4]#[C:5][C:6]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:7]=2[C:8](=[O:9])[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 86087094HCID 86087094, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 68534812HCID 68534812, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(Cyclopropylethynyl)-N-methyl-N,4-bis(methyloxy)benzamide (150) (0.47 g, 1.82 mmol) was treated with benzylmagnesium chloride in THF to give 0.47 g (89%) of the title compound (151) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 0.80-0.95 (m, 4H), 1.45-1.55 (m, 1H), 3.82 (s, 3H), 4.41 (s, 2H), 6.80 (dd, J1=8.8 Hz, J2=2.6 Hz, 1H), 6.94 (d, J=2.5 Hz, 1H), 7.20-7.26 (m, 3H), 7.27-7.33 (m, 2H), 7.65 (d, J=8.8 Hz, 1H). LCMS (ESI): m/z 291 (M+H)+.

Sources & evidence

ORD record
ord-d1b0184ab6e146daa2cd84c6eefc85b5
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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