Cesium carbonate → (5-Phenylfuran-2-yl)methanol

HRID 1532859Notes

Reaction equation

HRID 1532859 reaction equation
Br[C:2]1[O:6][C:5]([CH2:7][OH:8])=[CH:4][CH:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[C:9]1([C:2]2[O:6][C:5]([CH2:7][OH:8])=[CH:4][CH:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 14595701(5-Bromofuran-2-yl)methanol

Product 1

HCID 960786(5-Phenylfuran-2-yl)methanolYield 35%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

The 5-bromo-2-hydroxymethylfuran prepared in Example 327A (1.012 g, 5.72 mmol) was dissolved in 10 mL of DMF and PdCl2 (PPh3)2 (401 mg, 0.57 mmol) was added followed by phenylboronic acid (1.39 g, 11.4 mmol) and Cs2CO3 (3.71 g, 11.4 mmol) and the reaction was heated at 80° C. under N2 for 12 hours. The reaction mixture was taken up in ethyl acetate and washed with water (3×) and brine (3×), dried over Na2SO4, filtered and evaporated to a brown oil that was purified by flash chromatography (50% ethyl acetate-hexanes) to give the desired compound (345 mg, 35%) as an oil.

Workup

  1. washwashed with water (3×) and brine (3×)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to a brown oil that
  5. customwas purified by flash chromatography (50% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-d772a95ad09e4aa49ae1cf025dc407e5
Source dataset
uspto-grants-2001_03
Patent number
US06204293B1

Reaction notes

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