Triethylamine → HCID 12245491, compound

HRID 1010503Notes

Reaction equation

HRID 1010503 reaction equation
[O:1]([CH3:13])[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].CO[CH:16](OC)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(OCC)(=O)C.C(N(CC)CC)C>C(#N)C.CCCCCC.[NH4+].[NH4+].[O-][Mo]([O-])(=O)=O.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>[CH3:13][O:1][C@@H:2]1[O:10][C@@H:9]2[CH2:11][O:12][CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:8][C@H:7]2[C@H:5]([OH:6])[C@H:3]1[OH:4]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 62375Benzaldehyde dimethyl acetalHCID 445238Methyl beta-D-glucopyranoside

Product 1

HCID 12245491HCID 12245491, compoundYield 91.4%

Reagents, catalysts & solvents 4

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-CatalystHCID 61578Diammonium molybdateCatalystHCID 6342AcetonitrileSolventHCID 8058HexaneSolvent

Procedure

Using a modification of the procedure as described: Tetrahedron, 1992, 48(47), 10249-10264. Methyl β-D-glucopyranoside (Biosynth International M-3592; 10.2 g, 50 mmol), benzaldehyde dimethylacetal (30 ml, 200 mmol) and 10-camphorsulfonic acid (116 mg, 0.5 mmol) in anhydrous acetonitrile (150 ml) was stirred at room temperature for 4 h. The reaction was checked by TLC to confirm complete conversion to the product (run in hexane: ethyl acetate, 1:2, visualised with ceric ammonium molybdate spray and heating. The reaction was then treated with triethylamine (1 ml) to neutralise the acid. The solution was filtered and the solid was washed with acetonitrile (20 ml). The mother solution was concentrated to about 60 ml, and it was again filtrated, and the filtrate washed with acetonitdrile (10 ml). The combined solid was dried in vacuum, to give 12.9 g (91%) of methyl 4,6-O-benzylidene-β-D-glucopyranoside.

Workup

  1. temperatureheating
  2. filtrationThe solution was filtered
  3. washthe solid was washed with acetonitrile (20 ml)
  4. concentrationThe mother solution was concentrated to about 60 ml, and it
  5. filtrationwas again filtrated
  6. washthe filtrate washed with acetonitdrile (10 ml)
  7. customThe combined solid was dried in vacuum

Sources & evidence

ORD record
ord-a901cc318ff140d2bb71347f663afade
Source dataset
uspto-grants-2011_07
Patent number
US07976824B2

Reaction notes

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