Phenol → HCID 178527045, compound

HRID 1993110Notes

Reaction equation

HRID 1993110 reaction equation
C1(O)C=CC=CC=1.FC(F)(F)S(OC[P:15]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[PH:15](=[O:24])([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 10764777HCID 10764777, compound

Product 1

HCID 178527045HCID 178527045, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of phenol 17 (123 mg, 0.19 mmol) and dibenzyl trifluoromethansulfonyloxymethanphosphonate YY (120 mg, 0.28 mmol) in CH3CN (1.5 mL) at room temperature was treated Cs2CO3 (124 mg, 0.38 mmol). The mixture was stirred for 3 h and partitioned in CH2Cl2 and saturated NaHCO3. The organic layer was washed with 0.1N HCl, saturated NaCl, dried (MgSO4), filtered and evaporated under reduced pressure. The crude product was purified by chromatography on silica gel (10% MeOH/CH2Cl2) affording phosphonate 18 (154 mg, 88%). 1H NMR (CDCl3) δ 7.96 (s, 1H), 7.68 (d, 2H), 7.35 (m, 10H), 7.10 (d, 2H), 6.97 (d, 2H), 6.80 (d, 2H), 5.63 (d, 1H), 4.96-5.24 (m, 6H), 4.37 (m, 1H), 4.20 (d, 2H), 3.84 (s, 3H), 3.52-3.95 (m, 7H), 2.55-3.20 (m, 8H), 1.48-2.00 (m, 7H), 1.02 (m, 2H). 31P NMR (CDCl3) δ 20.3.

Workup

  1. custompartitioned in CH2Cl2
  2. washThe organic layer was washed with 0.1N HCl, saturated NaCl
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude product was purified by chromatography on silica gel (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-a97a0e613213402b804dd87411a90417
Source dataset
uspto-grants-2010_01
Patent number
US07649015B2

Reaction notes

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