Hydrochloric Acid → HCID 178472520, compound

A solution of ethyl 3-oxocyclobutanecarboxylate (2.90 g, 20.4 mmol, Parkway) in EtOH (30 mL) at ambient temperature was treated with NaBH4 (0.77 g, 20 mmol). The reaction was stirred for about 1 h and then 2 N aqueous HCl was added to adjust the pH to about 2. The reaction was concd in vacuo. The reaction was partitioned with DCM (50 mL) and brine (50 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered then concd in vacuo. The resulting residue was purified on silica gel (80 g) using 20-40% EtOAc in DCM to give cis-ethyl 3-hydroxycyclobutanecarboxylate (2.75 g, 66%) as a clear oil: 1H NMR (DMSO-d6) δ 5.17 (d, 1H), 4.09-3.99 (m, 2H), 3.99-3.90 (m, 1H), 2.57-2.47 (m, 1H), 2.42-2.29 (m, 2H), 1.98-1.89 (m, 2H), 1.17 (m, 3H).

1. customThe reaction was partitioned with DCM (50 mL) and brine (50 mL)
2. customThe organic layer was separated
3. dry with materialdried over anhydrous Na2SO4
4. filtrationfiltered
5. customThe resulting residue was purified on silica gel (80 g)

ORD record

ord-3288e074f5564ec9b1edbf7103d1c9df

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08426411B2