Hydrochloric Acid → HCID 178521042, compound

To a solution of ethyl cis-3-(4-fluorophenoxy)cyclobutanecarboxylate (5.07 g, 21.3 mmol) in dry methylene chloride (100 ml) cooled to -78° C. was added dropwise diisobutylaluminum hydride (23.7 ml, 22.0 mmol, 0.93M in hexane) under an argon atmosphere. After completion of addition, the mixture was stirred at the same temperature for 0.5 h. Methanol (5 ml) was carefully added to the reaction mixture at -78° C. and the whole allowed to warm to room temperature over 1 h. 2N aqueous hydrochloric acid (200 ml) was added, the whole extracted with ethyl acetate (300 ml) and the combined extracts washed with brine (200 ml). The organic layer was dried (MgSO4) and concentrated in vacuo. Chromatographic purification of the residue {SiO2, 300 g; hexane/ethyl acetate (4:1)} provided 3.20 g (78%) of title compound as a colorless oil: 1H NMR δ9.73 (d, J=2.6 Hz, 1H), 7.03-6.91 (m, 2H), 6.80-6.70 (m, 2H), 4.72-4.59 (m, 1H), 2.97-2.83 (m, 1H), 2.75-2.61 (m, 2H), 2.48-2.33 (m, 2H).

1. additionAfter completion of addition
2. extractionthe whole extracted with ethyl acetate (300 ml)
3. washthe combined extracts washed with brine (200 ml)
4. dry with materialThe organic layer was dried (MgSO4)
5. concentrationconcentrated in vacuo
6. customChromatographic purification of the residue {SiO2, 300 g

ORD record

ord-9f5409a746bd4502af336388d21b1264

Source dataset

uspto-grants-1997_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05681858