Toluene → HCID 86593010, compound
Reaction equation
[CH2:1]([P:4](=[O:7])([OH:6])[OH:5])[CH:2]=C.[C:8]1([OH:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[O:15]=S(Cl)Cl.[CH3:19][N:20]([CH:22]=[O:23])C.[C:24]1(C)C=CC=CC=1>>[C:8]1([O:6][P:4]([C:1]([CH3:2])([CH3:24])[CH2:19][NH2:20])(=[O:7])[OH:5])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:22]([OH:23])(=[O:15])[CH:8]([CH3:9])[OH:14]Participants
Conditions
- Temperature
- 65 °C
Procedure
To a solution of monophenol allylphosphonate 2 (4.75 g, 24 mmol) in toluene (30 mL) was added SOCl2 (5 mL, 68 mmol) and DMF (0.05 mL). After stirred at 65° C. for 4 h, the reaction was completed as shown by 31P NMR. The reaction mixture was evaporated and co-evaporated with toluene under reduced pressure to give mono chloride 3 (5.5 g) as an oil. To a solution of chloride 3 in CH2Cl2 (25 mL) at 0° C. was added ethyl(s)-lactate (3.3 mL, 28.8 mmol), followed by TEA. The mixture was stirred at 0° C. for 5 min then at room temperature for 1 h, and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and HCl (0.2N), the organic phase was washed with water, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to afford desired monolactate 4 (5.75 g, 80%) as an oil (2:1 mixture of two isomers): 1H NMR (CDCl3) δ 7.1-7.4 (m, 5H), 5.9 (m, 1H), 5.3 (m, 2H), 5.0 (m, 1H), 4.2 (m, 2H), 2.9 (m, 2H), 1.6; 1.4 (d, 3H), 1.25 (m, 3H); 31P NMR (CDCl3) δ 25.4, 23.9.
Workup
- customThe reaction mixture was evaporated
Sources & evidence
- ORD record
- ord-c5ac9df17a1c4329b4202bb05e43b3f6
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07649015B2
Reaction notes
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