Imidazole → (R)-3-(tert-butyldiphenylsilyloxy)dihydrofuran-2(3H)-one
Reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][O:4][C:3]1=[O:7].N1C=CN=C1.[Si:13](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[Si:13]([O:1][C@@H:2]1[CH2:6][CH2:5][O:4][C:3]1=[O:7])([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1Participants
Procedure
To a stirred solution of (R)-3-hydroxydihydrofuran-2(3H)-one (41.0 g, 401 mmol), imidazole (61.4 g, 920 mmol), and CH2Cl2 (175 mL) at 0° C., under N2, was added t-butyldiphenylsilyl chloride (129 mL, 138 g, 497 mmol) dropwise over 30 minutes. The mixture was stirred at room temperature for 19 hours. The mixture was partitioned between CH2Cl2 (700 mL) and H2O (100 mL). The organic portion was concentrated to dryness under reduced pressure. The residue was purified by silica gel chromatography (50% EtOAc in hexane) to afford (R)-3-(tert-butyldiphenylsilyloxy)dihydrofuran-2(3H)-one (127 g, 373 mmol, 93% yield) as a white solid. 1H-NMR (400 MHz, CDCl3) δ 7.84-7.82 (m, 2H), 7.73-7.71 (m, 2H), 7.50-7.40 (m, 6H), 4.41-4.31 (m, 2H), 4.06-4.00 (m, 1H), 2.29-2.19 (m, 2H), 1.10 (s, 9H).
Workup
- customThe mixture was partitioned between CH2Cl2 (700 mL) and H2O (100 mL)
- concentrationThe organic portion was concentrated to dryness under reduced pressure
- customThe residue was purified by silica gel chromatography (50% EtOAc in hexane)
Sources & evidence
- ORD record
- ord-8d269b2015564a11a68dea9e6661f03c
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07846954B2
Reaction notes
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