HCID 5370607, compound → HCID 11744782, compound

To a stirred suspension of LiAlH4 (2.4 g, 63.1 mmol) in dry Et2O (60 mL) at 0° C. under nitrogen atmosphere was added dropwise a solution of anhydrous AlCl3 (1.7 g, 12.6 mmol) in dry Et2O (30 mL). The reaction mixture was stirred at the same temperature for 30 min. To this stirred suspension, ester obtained in example 1 (8.0 g, 42.1 mmol) in dry Et2O (30 mL) was added dropwise over a period of 15 min and the resulting mixture stirred at 0° C. for 1 h. Then it was quenched with ice-water and filtered through celite and the residue was washed with ethyl acetate (3×30 mL). The combined organic layer was dried over anhydrous Na2SO4, concentrated, and the crude product was purified by column chromatography using petroleum ether/EtOAc (4:1) to afford the pure allylic alcohol 7 (5.4 g, 87%) as a colorless oil. IR: (CHCl3, cm−1): νmax 694, 744, 966, 1049, 1107, 1364, 1454, 2857, 2932, 3385; 1H NMR (200 MHz, CDCl3): δ 1.22 (br s, 1H), 3.38 (d, J=6.4 Hz, 2H), 4.12 (t, J=4.8 Hz, 2H), 5.62-5.93 (m, 2H), 7.15-7.32 (m, 5H); 13C NMR (50 MHz, CDCl3): δ 36.4, 61.9, 126.0, 126.3, 127.2, 128.5, 132.7, 137.2; Anal. Calcd for C10H12O: C, 81.04; H, 8.16. Found: C, 81.02; H, 8.15%.

1. stirringthe resulting mixture stirred at 0° C. for 1 h
2. customThen it was quenched with ice-water
3. filtrationfiltered through celite
4. washthe residue was washed with ethyl acetate (3×30 mL)
5. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
6. concentrationconcentrated
7. customthe crude product was purified by column chromatography

ORD record

ord-43c8051756f649159a412a8051c23c6c

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09233943B2