HCID 86087169, compound → HCID 68534724, compound

HRID 1992957Notes

Reaction equation

HRID 1992957 reaction equation
[C:1]([C:11]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:12]=1[C:13](N(C)OC)=[O:14])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH2:25]([Mg]Cl)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1>[C:1]([C:11]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:12]=1[C:13](=[O:14])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 86087169HCID 86087169, compoundHCID 178418336HCID 178418336, compound

Product 1

HCID 68534724HCID 68534724, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(1-Decyn-1-yl)-N-methyl-N,4-bis(methyloxy)benzamide (192) (0.80 g, 2.41 mmol) was treated with benzylmagnesium chloride in THF to give 0.80 g (91%) of compound 193 as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 0.85-0.90 (m, 3H), 1.20-1.37 (m, 8H), 1.40-1.50 (m, 2H), 1.55-1.65 (m, 2H), 2.45 (t, J=7.2 Hz, 2H), 3.83 (s, 3H), 4.45 (s, 2H), 6.83 (dd, J1=8.7 Hz, J2=2.7 Hz, 1H), 6.98 (d, J=2.8 Hz, 1H), 7.70-7.26 (m, 3H), 7.27-7.33 (m, 2H), 7.66 (d, J=8.8 Hz, 1H). LCMS (ESI): m/z 363 (M+H)+, m/z 361 (M−H)−.

Sources & evidence

ORD record
ord-9ccd7485337c49718ae22c9964dd1e1f
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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