Cesium carbonate → HCID 58209395, compound

HRID 1676001Notes

Reaction equation

HRID 1676001 reaction equation
[CH2:1]1[O:5][C@@H:4]2[C@H:6]([OH:9])[CH2:7][O:8][C@@H:3]2[C@@H:2]1[OH:10].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH:22]=[CH2:23]>CN(C=O)C.CCOC(C)=O>[CH2:23]([O:10][C@H:2]1[C@H:3]2[O:8][CH2:7][C@@H:6]([OH:9])[C@H:4]2[O:5][CH2:1]1)[CH2:22][CH2:21][CH2:20][CH:19]=[CH2:18]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 759066-Bromo-1-hexeneHCID 109756241,4:3,6-Dianhydro-D-mannitol

Product 1

HCID 58209395HCID 58209395, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,4:3,6-dianhydro-D-mannitol (4.00 g, 27.4 mmol) and Cs2CO3 (20.0 g, 60.2 mmol) in DMF (60 ml), 6-bromo-1-hexene (5.5 ml, 41.1 mmol), was added; the mixture was stirred at room temperature for 18 hrs. Then it was diluted with EtOAc and washed with a 5% solution of sodium dihydrogen phosphate (2×40 ml) and water (2×40 ml). The organic layer was dried over sodium sulfate, filtered, concentrated and purified by flash chromatography (Biotage SP1, EtOAc/n-hexane from 20 to 80%), affording the title compound.

Workup

  1. washwashed with a 5% solution of sodium dihydrogen phosphate (2×40 ml) and water (2×40 ml)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography (Biotage SP1, EtOAc/n-hexane from 20 to 80%)

Sources & evidence

ORD record
ord-73750ff91a9c4b29bddff46084e9f787
Source dataset
uspto-grants-2011_08
Patent number
US08003811B2

Reaction notes

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