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-Eintrag

ord-97acb658d8ad486180185fd68f6b56bc

Quelldatensatz

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07141578B2