Sodium ethoxide → HCID 44468079, compound

HRID 1642419Notes

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.[CH2:20]([O:24][C:25]1[C:32]([O:33][CH3:34])=[CH:31][CH:30]=[CH:29][C:26]=1[CH:27]=O)[CH:21]([CH3:23])[CH3:22].[O-]CC.[Na+]>>[CH2:20]([O:24][C:25]1[C:32]([O:33][CH3:34])=[CH:31][CH:30]=[CH:29][C:26]=1/[CH:27]=[CH: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:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=1)[CH:21]([CH3:23])[CH3:22]

Participants

Reactant 3

HCID 2723922Sodium ethoxide

HCID 137497933-Methoxy-2-(2-methylpropoxy)benzaldehyde

HCID 66752927HCID 66752927, compound

Product 1

HCID 44468079HCID 44468079, compoundYield 44.5%

Procedure

The title compound was prepared by the reaction of Intermediate 4 (350 mg, 1.325 mmol) with 2-isobutoxy-3-methoxybenzaldehyde (409 mg, 1.961 mmol) in presence of sodium ethoxide (178 mg, 2.264 mmol) according to the procedure described in Example 9 to give 270 mg of the desired product as a light yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 1.85 (d, J=3.9 Hz, 4H), 2.03 (d, J=7.8 Hz, 3H), 3.77 (s, 3H), 3.83 (d, J=6.3 Hz, 2H), 6.84 (d, J=15.6 Hz, 1H), 6.95-7.00 (m, 3H), 7.50-7.58 (m, 3H), 7.92-8.04 (m, 3H), 8.14 (d, J=15.3 Hz, 1H); ESI-MS (m/z) 470.45 (M+H)+.

Sources & evidence

ORD record: ord-97b85c95332a489ab3e1ce908c96b4ee
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119647B2

Reaction notes

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