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

A solution of n-BuLi (83.0 mL, 133 mmol, 1.6 M in hexanes) was added to a stirred solution of 2-methylfuran (10.0 mL, 111 mmol) 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 (8.30 mL, 166 mmol) 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 (2×250 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. Distillation at atmospheric pressure (170-185° C.) gave 10.1 g (80.3 mmol, 72%) of compound 21A 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 (2×250 mL)
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-329281b38f304cd28b540045ffbe167d

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07517904B2