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4-METHOXY-3-(2-PROPYNYLOXY)BENZENECARBALDEHYDE synthesis

3synthesis methods
-

Yield:145654-01-9 100%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 20; for 3 h;

Steps:

1 Step 1. Preparation of 4-methoxy-3- (prop-2-yn-1-yloxy) benzaldehyde (129-01) :

K2CO3 (1.1g, 8.0mmol) was added to a solution of 3-hydroxy-4-methoxybenzaldehyde (1g, 6.6mmol) and 3-bromoprop-1-yne (0.95g, 7.9mmol) in DMF (10mL) . The reaction mixture was stirred at room temperature for 3hrs. The reaction mixture was extracted by EtOAc and H2O 3 times. The organic layer was combined, washed with brine, dried over Na2SO4, concentrated and further purified by silica gel column chromatography (PE/EA 4/1) , to give 1.24g of 4-methoxy-3- (prop-2-yn-1-yloxy) benzaldehyde as a yellow oil (100) . 1H NMR (400Hz, CDCl3) δ 7.50-7.53 (m, 2H) , 7.00 (d, J8.0Hz, 1H) , 4.81 (d, J2.4Hz, 2H) , 3.95 (s, 3H) , 2, 53-2.55 (t, J2.4Hz, 1H) .

References:

WO2018/14802,2018,A1 Location in patent:Paragraph 0376

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