Tetrafluoroboric acid → HCID 86611024, compound

HRID 2245913Notes

Reaction equation

HRID 2245913 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:26][C@H:25]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:10]2[O:11][C:12](=[O:14])[CH3:13])[OH:9])=[CH:4][C:3]=1[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][C:40]2([CH2:45][OH:46])[CH2:44][CH2:43][CH2:42][CH2:41]2)=[CH:35][CH:34]=1.F[B-](F)(F)F.[H+].[CH3:53][Si](C=[N+]=[N-])(C)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:26][C@H:25]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:10]2[O:11][C:12](=[O:14])[CH3:13])[OH:9])=[CH:4][C:3]=1[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][C:40]2([CH2:45][O:46][CH3:53])[CH2:44][CH2:43][CH2:42][CH2:41]2)=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 28118Tetrafluoroboric acidHCID 167693TrimethylsilyldiazomethaneHCID 86611022HCID 86611022, compound

Product 1

HCID 86611024HCID 86611024, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-chloro-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-2-[4-(1-hydroxymethyl-cyclopent-1-yloxy)-benzyl]-benzene (0.56 g) in dichloromethane (4 mL) chilled in an ice-bath is added tetrafluoroboric acid (0.12 mL) and trimethylsilyldiazomethane (0.45 mL). The solution is stirred at ambient temperature for 1 h and then quenched with water. The resultant mixture is extracted with dichloromethane, the combined extracts are dried (Na2SO4), the solvent is removed and the residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:0→2:1).

Workup

  1. customquenched with water
  2. extractionThe resultant mixture is extracted with dichloromethane
  3. dry with materialthe combined extracts are dried (Na2SO4)
  4. customthe solvent is removed
  5. customthe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:0→2:1)

Sources & evidence

ORD record
ord-8b0ed94bc9a943928f56cc416456ed1e
Source dataset
uspto-grants-2010_03
Patent number
US07683160B2

Reaction notes

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