Cesium carbonate → HCID 87315984, compound

HRID 2273740Notes

Reaction equation

HRID 2273740 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH:15]=[O:16])=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.Br[CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[Si:21]([O:20][CH2:19][CH2:18][O:14][C:11]1[CH:10]=[C:9]([CH:15]=[O:16])[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[CH:13][CH:12]=1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 86642871HCID 86642871, compound

Product 1

HCID 87315984HCID 87315984, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of EXAMPLE 125A (0.5 g), (2-bromoethoxy)(tert-butyl)dimethylsilane (0.771 g) and cesium carbonate (1.4 g) was suspended in anhydrous N,N-dimethylformamide (5 mL). The reaction mixture was heated at 70° C. overnight. The reaction mixture was cooled to room temperature and diluted with ethyl acetate. The organic phase was washed with water, brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude material was purified by flash column purification with 0-5% ethyl acetate/hexane to afford the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash column purification with 0-5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-785418be0eb84b0a84ab6059551d78b5
Source dataset
uspto-grants-2015_09
Patent number
US09125913B2

Reaction notes

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