Lets talk about ethers. Ethers that are small are water soluble. Dimethyl ether and ethyl methyl ether are water soluble. Once you reach 4 carbons,,,,,such as in diethyl ether, solubility drops off......diethyl ether has a solubility that is about 10g/100ml water. THF,,,the cyclic ether is an exception....it has 4 carbons that are " tied back "......consequently it can hydrogen bond very well with water.
I have used THF, a 4 carbon ether with an oxygen in the middle...also called oxacyclopentane.... in polar solvents for many years,,,,,,it dissolves wonderfully !!! As the carbon chain increases, it becomes more hydrocarbon-like. Thus larger ethers are not water soluble,
Hope this helps
Dr. Romano