Hydrogen Peroxide → HCID 70478770, compound

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Reaction Steps

A dihydro-2H-pyran-2-ylmethoxy ether of Formula 1 is an especially useful intermediate to the ethers of formula 1 in which R is, e.g. hydroxy, oxo, methylene, alkyl or alkoxy by use of conventional synthesis techniques. For example, (3,4-dihydro-2H-pyran-2-yl)methanol ether is treated with, e.g. borane in tetrahydrofuran followed by hydrogen peroxide and sodium hydroxide, to give the corresponding (3,4,5,6-tetrahydro-5-hydroxy-2H-pyran-2-yl)methanol ether. This hydroxy ether is treated with, e.g. oxalyl chloride in dimethyl sulfoxide, to obtain the corresponding (3,4,5,6-tetrahydro-2H-5-oxo-pyran-2-yl)methanol ether. This oxo ether is treated with, e.g. methyl triphenyl phosphonium bromide, to obtain the corresponding (3,4,5,6-tetrahydro-2H-5-methylene-pyran-2-yl)methanol ether. This ether is treated with, e.g. hydrogen in the presence of platinum oxide and ethyl acetate, to give the corresponding (3,4,5,6-tetrahydro-2H-5-methoxypyran-2-yl)methanol ether.

Provenance & Evidence