Triethylamine → HCID 86610216, compound

HRID 2263597Notes

Reaction equation

HRID 2263597 reaction equation
C(N(CC)CC)C.[CH3:8][Si:9]([C:12]#[CH:13])([CH3:11])[CH3:10].[C:14]([O:17][C@@H:18]1[C@@H:24]([O:25][C:26](=[O:28])[CH3:27])[C@H:23]([O:29][C:30](=[O:32])[CH3:31])[C@@H:22]([CH2:33][O:34][C:35](=[O:37])[CH3:36])[O:21][C@@:19]1([C:38]1[CH:43]=[CH:42][C:41]([CH3:44])=[C:40]([CH2:45][C:46]2[CH:51]=[CH:50][C:49](OS(C(F)(F)F)(=O)=O)=[CH:48][CH:47]=2)[CH:39]=1)[OH:20])(=[O:16])[CH3:15]>CN(C)C=O.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:14]([O:17][C@@H:18]1[C@@H:24]([O:25][C:26](=[O:28])[CH3:27])[C@H:23]([O:29][C:30](=[O:32])[CH3:31])[C@@H:22]([CH2:33][O:34][C:35](=[O:37])[CH3:36])[O:21][C@@:19]1([C:38]1[CH:43]=[CH:42][C:41]([CH3:44])=[C:40]([CH2:45][C:46]2[CH:51]=[CH:50][C:49]([C:13]#[C:12][Si:9]([CH3:11])([CH3:10])[CH3:8])=[CH:48][CH:47]=2)[CH:39]=1)[OH:20])(=[O:16])[CH3:15]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111Trimethylsilylacetylene2×HCID 86610217HCID 86610217, compound

Product 1

HCID 86610216HCID 86610216, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalyst2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Under argon, 17.3 mg copper iodide, 31.9 mg bis-(triphenylphosphine)-palladium dichloride, 0.22 ml triethylamine and finally 0.19 ml trimethylsilylacetylene are added to a solution of 0.30 g 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-3-[4-(trifluoromethylsulfonyloxy)-benzyl]-4-methyl-benzene in 1.5 ml of dimethylformamide. The flask is tightly sealed and stirred at 90° C. over night. After 4 h additional 20 mg bis-(triphenylphosphine)-palladium dichloride and 0.2 ml trimethylsilylacetylene are added, and the mixture is further stirred at 90° C. for 4 h. After cooling the reaction mixture to room temperature, the solvent is removed and the residue purified by chromatography on silica gel (cyclohexane/ethyl acetate 4:1->1:2).

Workup

  1. customThe flask is tightly sealed
  2. stirringthe mixture is further stirred at 90° C. for 4 h
  3. temperatureAfter cooling the reaction mixture to room temperature
  4. customthe solvent is removed
  5. customthe residue purified by chromatography on silica gel (cyclohexane/ethyl acetate 4:1->1:2)

Sources & evidence

ORD record
ord-41791a10d79c4d95b2225260b21a45ee
Source dataset
uspto-grants-2010_12
Patent number
US07851602B2

Reaction notes

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