Imidazole → 5-(3-((tert-butyldimethylsilyl)oxy)-2-hydroxypropyl)-4-methylisobenzofuran-1(3H)-one
Reaction equation
[OH:1][CH:2]([CH2:15][OH:16])[CH2:3][C:4]1[C:5]([CH3:14])=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[O:8][CH2:7]2.N1C=CN=C1.[CH3:22][C:23]([Si:26](Cl)([CH3:28])[CH3:27])([CH3:25])[CH3:24]>CN(C=O)C.C(Cl)Cl>[Si:26]([O:16][CH2:15][CH:2]([OH:1])[CH2:3][C:4]1[C:5]([CH3:14])=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[O:8][CH2:7]2)([C:23]([CH3:25])([CH3:24])[CH3:22])([CH3:28])[CH3:27]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 5-(2,3-dihydroxypropyl)-4-methylisobenzofuran-1(3H)-one (2.00 g, 9.0 mmol) in dry DMF (20 mL) was added imidazole (1.20 g, 18.0 mmol) and TBSCl (1.50 g, 9.9 mmol). After stirring at 25° C. for 2.5 h, the reaction mixture was diluted with CH2Cl2 (50 mL) and washed with H2O (3×20 mL) and saturated NaHCO3 (3×20 mL). The combined aqueous layers were extracted five times with CH2Cl2 (20 mL). The combined organic layers were washed with brine (3×30 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (0-60% ethyl acetate in petroleum ether) to give the title compound.
Workup
- washwashed with H2O (3×20 mL) and saturated NaHCO3 (3×20 mL)
- extractionThe combined aqueous layers were extracted five times with CH2Cl2 (20 mL)
- washThe combined organic layers were washed with brine (3×30 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash column chromatography (0-60% ethyl acetate in petroleum ether)
Sources & evidence
- ORD record
- ord-b2066a93780b4a7ca4a6c6bce8658d3f
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206198B2
Reaction notes
Loading…