Dichloromethane → 5-Benzyloxy-2-but-1-enylphenol

To a flame dried 500 mL 3-neck flask under an atmosphere of argon, was charged n-propyltriphenylphosphonium bromide (12.66 g, 32.85 mmol) dissolved in anhydrous THF (85 mL), followed by the dropwise addition of n-butyllithium 16.4 mL, 26.28 mmol). The dark red mixture was stirred at ambient temperature for 1 h. 15 min. Next 4-benzyloxy-2-hydroxybenzaldehyde (1.5 g, 6.57 mmol) (Synth. Commun., 26(3), 593-601, (1996) was added followed by the addition of anhydrous dichloromethane (27 mL). The mixture was stirred at ambient temperature for 18 h. The solvents were removed in vacuo, and the residue was partitioned between ethyl acetate and water (500 mL each). The organic layer was washed with brine (500 mL), dried (Na2SO4), and concentrated in vacuo. The crude product was purified using the Biotage FlashElute chromatography system using a 65M normal phase cartridge, eluting with 15% ethyl acetate/Hex to give a yellow solid (1.50 g, 90%). 1H NMR (400 MHz, CDCl3) δ 7.43-7.30 (m, 5H), 7.19 (d, J=8.3 Hz, 1H), 6.52 (dd, J=8.8, 2.4 Hz, H), 6.46 (d, J=2.4 Hz, 1H), 6.43 (s, 1H), 6.14-6.07 (m, 1H), 5.03 (s, 2H), 4.98 (s, 1H), 2.25 (quintet, J=7.6 Hz, 2H), 1.09 (t, J=7.3 Hz, 3H), MS (ES) m/e 255 (M+1).

1. customTo a flame dried 500 mL 3-neck flask under an atmosphere of argon
2. custom15 min
3. addition, 26(3), 593-601, (1996) was added
4. stirringThe mixture was stirred at ambient temperature for 18 h
5. customThe solvents were removed in vacuo
6. customthe residue was partitioned between ethyl acetate and water (500 mL each)
7. washThe organic layer was washed with brine (500 mL)
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated in vacuo
10. customThe crude product was purified
11. washeluting with 15% ethyl acetate/Hex

ORD record

ord-afbaf7274ff145d7b32e79eb7c917621

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06825222B2