Dichloromethane → Dihydrobenzofuran

Temperature

10 °C

A flame dried 1-liter, 3-neck flask fitted with a dropping funnel, mechanical stirrer, N2 inlet, and an internal thermometer was charged with 5-benzyloxy-6-hydroxymethyl-2,3-dihydrobenzofuran (28.90 g, 0.11 moles), methylene chloride (250 ml) and triethylamine (16 ml, 0.11 moles). The reaction mixture was chilled to 10° C. and methanesulfonyl chloride (8.9 ml, 0.11 mole) was added dropwise, while maintaining an internal reaction temperature of 10° C. The resultant yellow-green mixture was warmed to room temperature and stirred for 15 hours. Water (100 ml) was added to the reaction, the layers partitioned and separated. The organic phase was washed sequentially with saturated sodium bicarbonate solution (2×100 ml) and brine (1×100 ml) to remove some greenish color. The yellow organic layear was dried over MgSO4, suction filtered and the filtrate concentrated in vacuo to afford 5-benzyloxy-6-methanesulfonyloxymethyl)-2,3-dihydrobenzofuran a yellow precipitate (33.0 g, 88%). The crude product was used in the next step without further purification which was not necessary for the subsequent reaction.

1. customA flame dried 1-liter, 3-neck flask
2. customfitted with a dropping funnel, mechanical stirrer, N2 inlet
3. temperaturewhile maintaining an internal reaction temperature of 10° C
4. temperatureThe resultant yellow-green mixture was warmed to room temperature
5. customthe layers partitioned
6. customseparated
7. washThe organic phase was washed sequentially with saturated sodium bicarbonate solution (2×100 ml) and brine (1×100 ml)
8. customto remove some greenish color
9. dry with materialThe yellow organic layear was dried over MgSO4, suction
10. filtrationfiltered
11. concentrationthe filtrate concentrated in vacuo

ORD record

ord-721a6d5903d24bb59ef671971371e42d

Source dataset

uspto-grants-1988_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04775679