3-Methoxybenzaldehyde → 2-{4-[2-(3-Methoxyphenyl)-vinyl]-phenyl}-6-methylbenzothiazole

HRID 339591Notes

Reaction equation

HRID 339591 reaction equation
CO[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.[CH3:27]C(C)([O-])C.[K+].[CH3:33][O:34][C:35]1[CH:36]=[C:37]([CH:40]=[CH:41][CH:42]=1)[CH:38]=O.CCCCCC.CCOCC>C1COCC1>[CH3:33][O:34][C:35]1[CH:36]=[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]([CH3:27])[CH:26]=[CH:25][C:6]=4[N:7]=3)=[CH:24][CH:23]=2)[CH:40]=[CH:41][CH:42]=1

Participants

6

Reactant 4

HCID 115693-MethoxybenzaldehydeHCID 13599215Diethyl 4-(6-methoxybenzothiazol-2-yl)benzylphosphonateHCID 21584099Diethylether hexaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 672381492-{4-[2-(3-Methoxyphenyl)-vinyl]-phenyl}-6-methylbenzothiazoleYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Prepared as described in the Alkene Formation section using diethyl 4-(6-methoxybenzothiazol-2-yl)benzylphosphonate (0.05 g, 0.133 mmol) in dry THF (5 ml), potassium t-butoxide (0.03 g, 0.266 mmol) and 3-methoxybenzaldehyde (0.018 g, 0.133 mmol) in dry THF (5 ml) to give the title compound (0.016 g, 34%) as a yellow solid after work-up and flash chromatography (4:1 Hexane/Et2O).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-a7ec45735c444757a2c182c11aaf19e5
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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