Ethanol → 4-Chloroacetoxy-4-methyltetrahydropyran

A four-necked flask having an inner volume of 100 mL, which was equipped with a dropping funnel, a thermometer and a nitrogen introducing pipe, was charged with 4.64 g (40.0 mmoles) of 4-hydroxy-4-methyltetrahydropyran and 20.0 g of methylene chloride and further charged with 0.24 g (2.0 mmoles) of 4-(N,N-dimethylamino)pyridine and 6.78 g (60.0 mmoles) of 2-chloroacetyl chloride. Subsequently, 6.37 g (63.0 mmoles) of triethylamine was added dropwise at room temperature over 30 minutes. After completion of the dropwise addition, the mixture was stirred at room temperature for 10 hours. To this reaction mixed solution, 1.11 g (24.0 mmoles) of ethanol was added dropwise, and subsequently, 20.0 g of water was added dropwise; and the mixture was stirred for 20 minutes. This reaction mixed solution was separated into an aqueous layer and an organic layer. The aqueous layer was extracted twice with 20 mL of methylene chloride; the extract was combined with the foregoing organic layer; the mixture was washed once with 10 mL of water and concentrated in vacuo, thereby obtaining 6.09 g (31.6 mmoles) of 4-chloroacetoxy-4-methyltetrahydropyran (yield: 79%).

1. customA four-necked flask having
2. customan inner volume of 100 mL, which was equipped with a dropping funnel
3. additionAfter completion of the dropwise addition
4. additionwas added dropwise
5. stirringand the mixture was stirred for 20 minutes
6. additionThis reaction mixed solution
7. customwas separated into an aqueous layer
8. extractionThe aqueous layer was extracted twice with 20 mL of methylene chloride
9. washthe mixture was washed once with 10 mL of water
10. concentrationconcentrated in vacuo

ORD record

ord-15e646a1ebbd4058bd07673e412b6c8a

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07867690B2