Water → 2H-Pyran, 3,4-dihydro-6-[(phenylmethoxy)methyl]-

A solution of 5.71 g of 6-hydroxymethyl-3,4-dihydro-2H-pyran dissolved in 100 ml of dimethylformamide was added dropwise to a mixture of 2.18 g of sodium hydride (as a 55% w/w dispersion in mineral oil) and dimethylformamide, whilst ice-cooling. The mixture was then stirred at room temperature for 1 hour, after which 6.33 g of benzyl chloride were added to it. The mixture was stirred for 16 hours, after which it was poured into 1 liter of water. The resulting mixture was then extracted twice with ethyl acetate. The combined extracts were washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The oily residue (13 g) was subjected to column chromatography through 200 g of silica gel. 9.40 g of the title compound were obtained as a colorless oil from those fractions eluted with mixtures of diethyl ether and hexane ranging from 4:100 to 5:100 by volume. It boiled at 125°-130° C. (bath temperature)/1 mmHg (133 Pa).

1. temperaturewhilst ice-cooling
2. stirringThe mixture was stirred for 16 hours
3. extractionThe resulting mixture was then extracted twice with ethyl acetate
4. washThe combined extracts were washed with water
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated by evaporation under reduced pressure

ORD record

ord-6e4af5ddfc164d82987515a31354fa1c

Source dataset

uspto-grants-1990_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04891363