반응 #59886

반응 방정식

2-(hydroxymethyl)-1,3-propanediol

tetrahydro-4H-pyran-4-one

benzene

→

title compound

수율 64.9%

1,5,9-trioxaspiro[5.5]undec-3-ylmethanol

수율 64.9%

용매

triethylamine

반응 조건

후처리

1. 1
   온도was refluxed in a round bottom flask
2. 2
   기타equipped with a cooling tube
3. 3
   농축the mixture was concentrated
4. 4
   기타The residue was purified by silica gel column chromatography (silica gel: 200 g, elution solvent: heptane, heptane/ethyl acetate=1/1, 1/3)

실험 절차

A mixture of 2-(hydroxymethyl)-1,3-propanediol (3.3 g, 31.1 mmol), tetrahydro-4H-pyran-4-one (3.12 g, 31.2 mmol), p-toluenesulfonic acid monohydrate (268 mg, 1.41 mmol) and benzene (68.3 ml) was refluxed in a round bottom flask equipped with a cooling tube and Dean-Stark for 6 hours. After cooled to room temperature, triethylamine (1 ml) was added to the reaction mixture and the mixture was concentrated. The residue was purified by silica gel column chromatography (silica gel: 200 g, elution solvent: heptane, heptane/ethyl acetate=1/1, 1/3) to obtain the title compound (3.80 g, yield: 64.9%) as a colorless oil.

출처