3,4-dihydro-2H-pyran → HCID 86654333, compound

HRID 45823Notes

Reaction equation

HRID 45823 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[CH3:7][O:8][P:9]([CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[N:22])[CH:16]=1)[OH:14])(=[O:12])[O:10][CH3:11]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:7][O:8][P:9]([CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[N:22])[CH:16]=1)[O:14][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][O:1]1)(=[O:12])[O:10][CH3:11]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 86654332(3-Cyanophenyl-hydroxy-methyl]-phosphonic acid dimethyl ester

Product 1

HCID 86654333HCID 86654333, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

3,4-Dihydro-2H-pyran (10.83 g, 128.70 mmol) and p-toluenesulfonic acid (0.34 g, 1.75 mmol) were added to a solution of [(3-cyanophenyl-hydroxy-methyl]-phosphonic acid dimethyl ester (14.10 g, 58.50 mmol) in dry toluene (195 ml) and the reaction mixture was stirred under nitrogen atmosphere at 50° C. for 3 h. The solvent was then removed under vacuum and the residue was taken up with ethyl acetate (100 ml). The organic layer was washed with a saturated NaHCO3 solution (1×100 ml), brine (1×100 ml) and dried over Na2SO4. The filtrate was evaporated to dryness to give the crude [(3-cyano-phenyl)-(tetrahydro-pyran-2-yloxy)-methyl]phosphonic acid dimethyl ester as a yellow oil (19 g, 58.46 mmol, 100%).

Workup

  1. customThe solvent was then removed under vacuum
  2. washThe organic layer was washed with a saturated NaHCO3 solution (1×100 ml), brine (1×100 ml)
  3. dry with materialdried over Na2SO4
  4. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-d6d1e3de49d34d43a7f4a3a30a59da05
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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