Imidazole → (R)-4-bromo-3-(2-((tert-butyldiphenylsilyl)oxy)-1-hydroxyethyl)-1H-isochromen-1-one

HRID 572479Notes

Reaction equation

HRID 572479 reaction equation
[Br:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5](=[O:12])[O:4][C:3]=1[C@H:13]([OH:16])[CH2:14][OH:15].N1C=CN=C1.[C:22]([Si:26]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)Cl)([CH3:25])([CH3:24])[CH3:23].O>CN(C)C=O>[Br:1][C:2]1[C:7]2[C:6](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:5](=[O:12])[O:4][C:3]=1[C@H:13]([OH:16])[CH2:14][O:15][Si:26]([C:22]([CH3:25])([CH3:24])[CH3:23])([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 68295550HCID 68295550, compound

Product 1

HCID 68294919(R)-4-bromo-3-(2-((tert-butyldiphenylsilyl)oxy)-1-hydroxyethyl)-1H-isochromen-1-oneYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-bromo-3-[(1R)-1,2-dihydroxyethyl]-1H-2-benzopyran-1-one (145 mg, 0.509 mmol) and imidazole (51.9 mg, 0.763 mmol) in N,N-Dimethylformamide (DMF) (2.4 mL) was treated with tert-butyldiphenylchlorosilane (159 μl, 0.610 mmol). After 20 min, the reaction mixture was poured into water and extracted with EtOAc. The organic phase was dried with Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (ethyl acetate-hexanes 0-50%) to afford the title compound (169 mg, 0.323 mmol, 64% yield) as a white foam: Rt=1.24 min, ES+ MS: 546 (M+23).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phase was dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (ethyl acetate-hexanes 0-50%)

Sources & evidence

ORD record
ord-0516b59dae244d6584d661b67123ff2a
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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