Sodium Methoxide → 2-{4-[2-(4-(2-Fluoroethoxy)-phenyl)-vinyl]-phenyl}-6-methoxybenzothiazole

HRID 339583Notes

Reaction equation

HRID 339583 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]2[N:7]=[C:8]([C:10]3[CH:24]=[CH:23][C:13]([CH2:14]P(=O)(OCC)OCC)=[CH:12][CH:11]=3)[S:9][C:5]=2[CH:4]=1.C[O-].[Na+].[F:30][CH2:31][CH2:32][O:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=1>CO>[F:30][CH2:31][CH2:32][O:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]=[CH:14][C:13]2[CH:12]=[CH:11][C:10]([C:8]3[S:9][C:5]4[CH:4]=[C:3]([O:2][CH3:1])[CH:26]=[CH:25][C:6]=4[N:7]=3)=[CH:24][CH:23]=2)=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 13599215Diethyl 4-(6-methoxybenzothiazol-2-yl)benzylphosphonateHCID 150586494-(2-Fluoroethoxy)benzaldehyde

Product 1

HCID 913081242-{4-[2-(4-(2-Fluoroethoxy)-phenyl)-vinyl]-phenyl}-6-methoxybenzothiazoleYield 77.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared as described in the Alkene Formation section using diethyl 4-(6-methoxybenzothiazol-2-yl)benzylphosphonate (0.06 g, 0.153 mmol), sodium methoxide (0.5 M solution in MeOH, 0.46 ml, 0.23 mmol) and 4-(2-fluoroethoxy)-benzaldehyde (0.028 g, 0.168 mmol) in dry MeOH (5 ml) to give the title compound (0.048 g, 77%) as a pale yellow solid after work-up.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-222c96cab62b4f7fb545f7194d37940d
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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