Sodium ethoxide → HCID 44467008, compound

HRID 1642423Notes

Reaction equation

HRID 1642423 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[S:19][CH:18]=[CH:17][N:5]2[C:6](=[O:16])[C:7]=1[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[CH:20]1([CH2:23][O:24][C:25]2[C:32]([O:33][CH3:34])=[CH:31][CH:30]=[CH:29][C:26]=2[CH:27]=O)[CH2:22][CH2:21]1.[O-]CC.[Na+]>C(O)C>[CH:20]1([CH2:23][O:24][C:25]2[C:32]([O:33][CH3:34])=[CH:31][CH:30]=[CH:29][C:26]=2/[CH:27]=[CH:1]/[C:2]2[N:3]=[C:4]3[S:19][CH:18]=[CH:17][N:5]3[C:6](=[O:16])[C:7]=2[C:8]2[CH:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=2)[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 435604072-(Cyclopropylmethoxy)-3-methoxybenzaldehydeHCID 66752927HCID 66752927, compound

Product 1

HCID 44467008HCID 44467008, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared from Intermediate 4 (180 mg, 0.673 mmol), 2-(cyclopropylmethoxy)-3-methoxybenzaldehyde (192 mg, 1.010 mmol) and sodium ethoxide (92 mg, 1.346 mmol) in ethanol (15 ml) according to the procedure described in Example 9 to give 135 mg of the product as a light yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 0.25-0.27 (m, 2H), 0.49-0.51 (m, 2H), 0.90-1.10 (m, 1H), 3.68 (d, J=7.8 Hz, 2H), 3.77 (s, 3H), 6.85 (d, J=15.6 Hz, 1H), 6.96-7.00 (m, 3H), 7.51-7.57 (m, 3H), 7.92 (d, J=7.8 Hz, 2H), 8.01 (d, J=5.1 Hz, 2H), 8.17 (d, J=15.6 Hz, 1H); ESI-MS (m/z) 456.23 (M+H)+.

Sources & evidence

ORD record
ord-5b13fa3e731c43c0a3f2c75e07bc7349
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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