p-Toluenesulfonic acid → HCID 86654330, compound

HRID 1843600Notes

Reaction equation

HRID 1843600 reaction equation
[CH3:1][O:2][P:3]([CH:7]([OH:17])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=1)(=[O:6])[O:4][CH3:5].[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][P:3]([CH:7]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=1)[O:17][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][O:18]1)(=[O:6])[O:4][CH3:5]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 11299958[Hydroxy-(3-nitro-phenyl)methyl]-phosphonic acid dimethyl ester

Product 1

HCID 86654330HCID 86654330, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

[Hydroxy-(3-nitro-phenyl)-methyl]-phosphonic acid dimethyl ester (26.7 g, 0.102 mol) was suspended in dry toluene (340 mL) under nitrogen atmosphere. 3,4-Dihydro-2H-pyrane (20.6 mL, 0.228 mol, 2.2 eq) was added, followed by p-toluensulfonic acid (590 mg, 0.003 mol, 0.03 eq) and the mixture was stirred at 60° C. for 1 h. the reaction mixture was then concentrated under reduced pressure, taken up with ethyl acetate (300 mL) and washed with saturated aqueous NaHCO3 and water. The organic layer was dried over Na2SO4 and concentrated to dryness. The desired product was obtained in quantitative yield as a yellow solid (mixture of 2 diastereoisomers).

Workup

  1. concentrationwas then concentrated under reduced pressure
  2. washwashed with saturated aqueous NaHCO3 and water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-690cf64fb49547198403f5b2c95869d3
Source dataset
uspto-grants-2015_02
Patent number
US08946250B2

Reaction notes

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