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37414-44-1

1H-Indene-2-carboxaldehyde, 2,3-dihydro- (9CI) synthesis

8synthesis methods
-

Yield:37414-44-1 96%

Reaction Conditions:

with Dess-Martin periodane in dichloromethane at 20; for 4 h;

Steps:

1 Example 1

[000259] A solution of Compound IB (200 mg, 1.4 mmol) and Dess-Martin reagent (688 mg, 1.6 mmol) in dichloromethane (20 mL) was stirred at rt for 4 h. The resulting solution was poured into a saturated solution of sodium hydrogen carbonate (20 mL) in which beforehand sodium thiosulfate pentahydrate had been dissolved. After 15 min of vigorous stirring, the organic phase was collected and the aqueous phase was extracted with diethyl ether (10 mL x 3). The combined organic layers were dried and evaporated to give a crude product which was purified by column chromatography on silica gel (ethyl acetate in petroleum ether, from 1% to 4% v/v) to afford Compound 1C (190 mg, yield 96%>) as a yellow oil. 1H-NMR (CDC13, 400 MHz) major characteristic peaks: δ (ppm) 3.05-3.23 (m,5H), 7.06-7.15 (m, 4 H), 9.67 (s,lH).

References:

WO2015/42397,2015,A1 Location in patent:Paragraph 000259