Cesium carbonate → HCID 57643428, compound

HRID 2113167Notes

Reaction equation

HRID 2113167 reaction equation
[CH2:1]([C@@:3]1([C:13]([O:15][CH3:16])=[O:14])[CH2:7][C:6]2[CH:8]=[C:9]([OH:12])[CH:10]=[CH:11][C:5]=2[O:4]1)[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[CH3:16][O:15][C:13]([C@:3]1([CH2:1][CH3:2])[CH2:7][C:6]2[CH:8]=[C:9]([O:12][CH2:7][CH2:3][CH:1]=[CH2:2])[CH:10]=[CH:11][C:5]=2[O:4]1)=[O:14]

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 11148763HCID 11148763, compound

Product 1

HCID 57643428HCID 57643428, compoundYield 101.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl (2S)-2-ethyl-5-hydroxy-2,3-dihydro-benzofuran-2-carboxylate (0.22 g, 1.0 mmol), prepared in Example 10, Step 2,4-bromo-1-butene (1.35 g, 10 mmol) and Cs2CO3 (1.63 g, 5.0 mmol) in DMF (20 mL) was stirred at 50° C. for 16 hrs. The reaction was diluted with ethyl acetate and washed with water. After removal of the solvent, the reisdue was purified by preparative TLC to give 0.14 g (2S)-5-But-3-enyloxy-2-ethyl-2,3-dihydro-benzofuran-2Carboxylic acid methyl ester.

Workup

  1. washwashed with water
  2. customAfter removal of the solvent
  3. customthe reisdue was purified by preparative TLC

Sources & evidence

ORD record
ord-bc8f340136254757ab20e58e1eb52282
Source dataset
uspto-grants-2009_04
Patent number
US07524882B2

Reaction notes

Loading…