Bromotrimethylsilane → HCID 69015383, compound

HRID 916602Notes

Reaction equation

HRID 916602 reaction equation
[C@@H:1]1([O:12][C:13]2[C:18]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][O:28]COC)=[CH:22][CH:21]=3)=[C:17]([CH3:32])[CH:16]=[C:15]([CH3:33])[N:14]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].C[Si](C)(C)Br.C(=O)(O)[O-].[Na+]>ClCCl>[C@@H:1]1([O:12][C:13]2[C:18]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][OH:28])=[CH:22][CH:21]=3)=[C:17]([CH3:32])[CH:16]=[C:15]([CH3:33])[N:14]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3]

Participants

5

Reactant 3

HCID 76113BromotrimethylsilaneHCID 516892Sodium BicarbonateHCID 69422865HCID 69422865, compound

Product 1

HCID 69015383HCID 69015383, compoundYield 16.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(β-D-glucopyranosyloxy)-3-[4-(2-methoxymethyloxyethyl)benzyl]-4,6-dimethylpyridine (0.054 g) in dichloromethane (1.2 mL) was trimethylbromosilane (0.061 mL) at −23° C., and the mixture was stirred for 10 minutes. To the reaction mixture was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by preparative thin layer chromatography on silica gel (developing solvent: dichloromethane/methanol=6/1) to give 2-(β-D-glucopyranosyloxy)-3-[4-(2-hydroxyethyl)benzyl]-4,6-dimethylpyridine (0.008 g).

Workup

  1. customat −23° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by preparative thin layer chromatography on silica gel (developing solvent: dichloromethane/methanol=6/1)

Sources & evidence

ORD record
ord-0a697495cf2a4108bc728aaac11cae4b
Source dataset
uspto-grants-2007_09
Patent number
US07271153B2

Reaction notes

Loading…