Potassium Fluoride → [1-Hydroxy-3-(naphthalen-1-yl)-propyl]phosphonic acid dibenzyl ester

HRID 1080616Notes

Reaction equation

HRID 1080616 reaction equation
[C:1]1([CH2:11][CH2:12][CH:13]=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[P:15]([O-:32])([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[F-].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH2:25]([O:24][P:15]([CH:13]([OH:14])[CH2:12][CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)(=[O:32])[O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 110414091-NaphthalenepropanalHCID 21904359Dibenzylphosphite

Product 1

HCID 54410857[1-Hydroxy-3-(naphthalen-1-yl)-propyl]phosphonic acid dibenzyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3-(naphthalen-1-yl)propanal (2.3 g, 12.5 mmol) in DMF (6 mL) under nitrogen is added dibenzyl phosphite (3.3 g, 12.5 mmol), followed by potassium fluoride (0.94 g, 16.2 mmol). After 2 hours, the stirred suspension is diluted with ethyl acetate (60 mL) and washed with water (3×20 mL). The organic layer is dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel, eluting with a gradient of ethyl acetate in hexane (30% to 40% ). Concentration of the pure fractions in vacuo yields [1-hydroxy-3-(naphthalen-1-yl)-propyl]phosphonic acid dibenzyl ester as an oil which solidifies on standing.

Workup

  1. washwashed with water (3×20 mL)
  2. dry with materialThe organic layer is dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash-chromatography on silica gel
  6. washeluting with a gradient of ethyl acetate in hexane (30% to 40% )

Sources & evidence

ORD record
ord-ad062643ced140719e52ce174da4b842
Source dataset
uspto-grants-1996_12
Patent number
US05583123

Reaction notes

Loading…