Aluminium lithium hydride → (5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-yl)methanol

To a solution of ethyl 5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-carboxylate (600 mg, 2.27 mmol) in THF (10 mL) was added LiAlH4 (1M in THF, 2.72 mL, 2.72 mmol) at −20° C., the reaction was stirred at −20° C. for 30 min, and was quenched with Sat. NH4Cl, the aqueous layer was extracted with EtOAc, the combined organics were washed with brine, dried and concentrated to give crude oil, which was purified by column (Hexanes/EtOAc=100:0 to 20:80) to give (5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-yl)methanol (500 mg).

1. customwas quenched with Sat. NH4Cl
2. extractionthe aqueous layer was extracted with EtOAc
3. washthe combined organics were washed with brine
4. customdried
5. concentrationconcentrated
6. customto give crude oil, which
7. customwas purified by column (Hexanes/EtOAc=100:0 to 20:80)

ORD-Eintrag

ord-0898f9270df4423da89a956595bb8a96

Quelldatensatz

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09248199B2