Imidazole → (R)-3-(tert-butyldiphenylsilyloxy)dihydrofuran-2(3H)-one

HRID 1098672

Reaction equation

HRID 1098672 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]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 71570702-Hydroxy-gamma-butyrolactone, (2R)-

Product 1

HCID 53797635(R)-3-(tert-butyldiphenylsilyloxy)dihydrofuran-2(3H)-oneYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. customThe mixture was partitioned between CH2Cl2 (700 mL) and H2O (100 mL)
  2. concentrationThe organic portion was concentrated to dryness under reduced pressure
  3. customThe residue was purified by silica gel chromatography (50% EtOAc in hexane)

Sources & evidence

ORD record
ord-a15e809fcb5e40ea8eff27833f304306
Source dataset
uspto-grants-2012_03
Patent number
US08143297B2

Linked notes

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