3,4-dihydro-2H-pyran → 2-(5-Bromopentyloxy)tetrahydro-2H-pyran

To 36 g of 5-bromopentan-1-ol were added 24.72 ml of 2,3-dihydropyran and 3 drops of phosphorus oxychloride under cooling in an ice bath, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with diethyl ether, washed with 5% aqueous potassium hydroxide, water, a saturated aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and hexane (1:19) as eluent to give 49.5 g of the subtitle compound having the following physical characteristics:

1. temperatureunder cooling in an ice bath
2. washwashed with 5% aqueous potassium hydroxide, water
3. dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulphate
4. concentrationconcentrated under reduced pressure
5. customThe residue was purified by column chromatography on silica gel using
6. additiona mixture of ethyl acetate and hexane (1:19) as eluent

ORD record

ord-963694e4650e47aba6e53ac71fff74c3

Source dataset

uspto-grants-1982_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04355170