Sodium ethoxide → HCID 44467387, compound

HRID 1642439Notes

Reaction equation

HRID 1642439 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15](=[O:16])[N:14]3[CH:17]=[CH:18][S:19][C:13]3=[N:12][C:11]=2[CH3:20])=[CH:6][CH:5]=1)[CH3:2].[CH:21]1([CH2:24][O:25][C:26]2[C:33]([O:34][CH3:35])=[CH:32][CH:31]=[CH:30][C:27]=2[CH:28]=O)[CH2:23][CH2:22]1.[O-]CC.[Na+]>C(O)C>[CH:21]1([CH2:24][O:25][C:26]2[C:33]([O:34][CH3:35])=[CH:32][CH:31]=[CH:30][C:27]=2/[CH:28]=[CH:20]/[C:11]2[N:12]=[C:13]3[S:19][CH:18]=[CH:17][N:14]3[C:15](=[O:16])[C:10]=2[C:7]2[CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[CH:9][CH:8]=2)[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 435604072-(Cyclopropylmethoxy)-3-methoxybenzaldehydeHCID 66753310HCID 66753310, compound

Product 1

HCID 44467387HCID 44467387, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared by condensation of Intermediate 10 (300 mg, 1.047 mmol) with 2-cyclopropylmethoxy-3-methoxybenzaldehyde (302 mg, 1.466 mmol) in presence of sodium ethoxide (142 mg, 2.090 mmol) in ethanol (10 ml) according to the procedure of Example 24 to afford 200 mg of the desired product as a pale yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 0.25-0.27 (m, 2H), 0.49-0.51 (m, 2H), 1.03-1.05 (m, 1H), 3.67-3.70 (m, 2H), 3.77-3.81 (m, 3H), 6.89-6.91 (m, 2H), 6.98-7.02 (m, 4H), 7.23-7.26 (m, 2H), 7.47-7.49 (m, 1H), 7.96-8.10 (m, 1H), 8.10-8.15 (m, 1H); ESI-MS (m/z) 461.39 (M+H)+.

Sources & evidence

ORD record
ord-0c9761e665e54c99aa48826f78f29554
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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