Methane → 5-Benzyloxy-2,3-dihydrobenzofuran-6-carboxaldehyde

温度

0 °C

A 2-liter, 3-neck flask equipped with a nitrogen inlet, internal thermometer, mechanical stirrer, and reflux condenser was charged with 5-hydroxy-2,3-dihydrobenzofuran-6-carboxaldehyde (50.00 g; 0.30 moles), benzylbromide (38.6 ml, 0.34 moles), and crushed anhydrous K2CO3 (165.84 g, 1.20 moles). The reaction mixture was refluxed for 16 hours, cooled to room termperature and suction filtered. The filtrate was concentrated in vacuo to afford a yellow solid. The solid was dissolved in methylene chloride (600 ml) and washed sequentially with 0.5 N sodium hydroxide solution (3×250 ml) and brine (2×250 ml). The organic phase was dried over MgSO4, suction filtered, and the filtrate concentrated in vacuo to yield a crude solid (85 g). The solid was dissolved in methylene chloride (300 ml)/n-hexane (200 ml), treated with charcoal and suction filtered through a bed of celite. The filtrate was evaporated in vacuo to approximately 300 ml and slowly cooled to 0° C. to produce yellowish flat needles (60 g, 78%).

1. customA 2-liter, 3-neck flask equipped with a nitrogen inlet
2. temperatureinternal thermometer, mechanical stirrer, and reflux condenser
3. temperatureThe reaction mixture was refluxed for 16 hours
4. temperaturecooled to room termperature and suction
5. filtrationfiltered
6. concentrationThe filtrate was concentrated in vacuo
7. customto afford a yellow solid
8. washwashed sequentially with 0.5 N sodium hydroxide solution (3×250 ml) and brine (2×250 ml)
9. dry with materialThe organic phase was dried over MgSO4, suction
10. filtrationfiltered
11. concentrationthe filtrate concentrated in vacuo
12. customto yield a crude solid (85 g)
13. filtrationfiltered through a bed of celite
14. customThe filtrate was evaporated in vacuo to approximately 300 ml

ORDレコード

ord-14d03e4040aa4dc1823cc3a6d19afd09

出典データセット

uspto-grants-1988_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04775679