Ethylene Oxide → 2-(5-Methylfuran-2-yl)ethan-1-ol

A solution of n-BuLi (83 mL, 133.0 mmol, 1.2 eq, 1.6 M in hexanes) was added to a stirred solution of 2-methylfuran (10 mL, 110.8 mmol, 1 eq) in THF (85 mL) at 0° C. under inert atmosphere. The reaction mixture was stirred for 4 h at room temperature then cooled to 0° C. Ethylene oxide (8.3 mL, 166.3 mmol, 1.5 eq) was added dropwise and the reaction mixture was allowed to warm to room temperature overnight. After quenching with saturated aqueous NH4Cl, the resulting layers were separated and the aqueous layer was extracted with Et2O (2×). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. Distillation at atmospheric pressure (170-185° C.) gave 10.13 g (80.3 mmol, 72%) of 5-methyl-2-furanethanol (2f(2)) as a light yellow oil:

1. temperaturethen cooled to 0° C
2. temperatureto warm to room temperature overnight
3. customAfter quenching with saturated aqueous NH4Cl
4. customthe resulting layers were separated
5. extractionthe aqueous layer was extracted with Et2O (2×)
6. dry with materialThe combined organic layers were dried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. distillationDistillation at atmospheric pressure (170-185° C.)

ORD record

ord-c67773a842d44d21a64959c4b7aa354a

Source dataset

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06960474B2