Tetrahydrofuran → HCID 67543610, compound

To a solution of (methoxymethyl)triphosphonium chloride (5.56 g, 16.21 mmol) in dry THF (13 mL) under inter atmosphere was added dropwise at 0° C. a solution of nBuLi in dry THF (22 mL, 21.62 mmol). The reaction mixture was stirred at room temperature for 1 h. Then, a solution of 3-bromobenzaldehyde (2.0 g; 10.81 mmol) in dry THF (20 mL) was added dropwise at 0° C. The reaction mixture was stirred at room temperature for 16 h. A saturated solution of NH4Cl was added and the crude product was extracted with EtOAc (2 times) and the organic layer was washed with water, then with a saturated solution of NaCl, dried over MgSO4 and concentrated. The final product was purified by silica gel chromatography using 10 to 15% EtOAc/cyclohexane as eluent to give III-a as yellow oil in 66% yield. 1H NMR (300 MHz, CDCl3) δ 7.79 (s, J=1.5 Hz, 1H), 7.48-7.24 (m, 5H), 7.20-7.12 (m, 2H), 7.06 (d, J=13.0 Hz, 1H), 6.19 (d, J=7.0 Hz, 1H), 5.75 (d, J=13.0 Hz, 1H), 5.17 (d, J=7.0 Hz, 1H), 3.82 (s, 3H), 3.71 (s, 3H).

1. stirringThe reaction mixture was stirred at room temperature for 16 h
2. extractionthe crude product was extracted with EtOAc (2 times)
3. washthe organic layer was washed with water
4. dry with materialwith a saturated solution of NaCl, dried over MgSO4
5. concentrationconcentrated
6. customThe final product was purified by silica gel chromatography
7. customto give III-a as yellow oil in 66% yield

ORD record

ord-597f8131913c4b07815f0ddb7cbae786

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09168245B2