Triphenylphosphine → HCID 68457750, compound

To a mixture of triphenylphosphine (1.18 g, 4.49 mmol, 1.1 equiv) and DEAD (0.76 mL, 0.85 g, 4.89 mmol, 1.2 equiv) in anhydrous THF (10 mL) was added 3-ethoxy-5-hydroxy-benzoic acid methyl ester (0.8 g, 4.08 mmol, 1.0 equiv; prepared as described in WO 99/05123 A1, Astra Pharmaceuticals Ltd.) and tetrahydro-pyran-4-ol (0.42 g, 4.08 mmol, 1.0 equiv), dissolved in THF (10 mL), at 0° C. under Ar. After stirring for 6 h, the solvent was partially removed by evaporation under reduced pressure, water (50 mL) added and the reaction mixture extracted with ethyl acetate (3×50 mL). The combined organic phases were dried over MgSO4, the solvent removed by evaporation under reduced pressure and the crude material yielding 0.64 g (56%) of the title compound which was directly used in the next step. 1H NMR (300 MHz, CDCl3): δ 1.32 (t, J=7.0 Hz, 3H), 1.67-1.72 (m, 2H), 1.91-1.97 (m, 2H), 3.48-3.53 (m, 2H), 3.81 (s, 3H), 3.85-3.91 (m, 2H), 3.96 (q, J=7.0 Hz, 2H), 4.40-4.44 (m, 1H), 6.56-6.58 (m, 1H), 7.08-7.10 (m, 2H). 13C NMR (75 MHz, CDCl3): δ 14.59, 31.68, 51.99, 63.69, 64.89, 71.86, 107.82, 108.06, 109.09, 131.98, 158.17, 160.05, 166.61. MS (ISP): 281.2 [M+H]+.

1. customthe solvent was partially removed by evaporation under reduced pressure, water (50 mL)
2. additionadded
3. extractionthe reaction mixture extracted with ethyl acetate (3×50 mL)
4. dry with materialThe combined organic phases were dried over MgSO4
5. customthe solvent removed by evaporation under reduced pressure

ORD record

ord-aff14f3e104f48058981cb85057f72d3

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07645753B2