Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 60102584, compound

HRID 1805920Notes

Reaction equation

HRID 1805920 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][CH2:10][P:11](=[O:28])([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CCO>[OH:7][CH2:8][CH2:9][CH2:10][P:11](=[O:28])([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86657395HCID 86657395, compound

Product 1

HCID 60102584HCID 60102584, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of dibenzyl [3-(tetrahydro-2H-pyran-2-yloxy)propyl]phosphonate (3.08 g, 7.62 mmol) and pyridiniurn p-toluenesulfonate (0.191 g, 0.762 mmol) in EtOH (76 mL) was stirred at 55° C. overnight. The reaction mixture was cooled to room temperature and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Biotage Horizon, 40M, Si, ˜30 mL/min, 100% hexanes for 360 mL, gradient to 100% EtOAc in hexanes over 3096 mL, 100% EtOAc for 3888 mL) to afford dibenzyl (3-hydroxypropyl)phosphonate. Rf=0.34 (EtOAc). LCMS calc.=321.13; found=321.04 (M+H)+. 1H NMR (500 MHz, CHCl3): δ 7.35-7.28 (m, 10 H); 5.02 (dd, J=11.9, 8.9 Hz, 2 H); 4.94 (dd, J=11.9, 8.0 Hz, 2 H); 3.60 (t, J=5.6 Hz, 2 H); 3.37 (s, 1 H); 1.90-1.75 (m, 4 H).

Workup

  1. concentrationconcentrated in vacuo
  2. customto give the crude product
  3. customThis was purified by flash chromatography (Biotage Horizon, 40M, Si, ˜30 mL/min, 100% hexanes for 360 mL, gradient to 100% EtOAc in hexanes over 3096 mL, 100% EtOAc for 3888 mL)

Sources & evidence

ORD record
ord-78609721fc0b467e874f0f4e014a3ad5
Source dataset
uspto-grants-2013_01
Patent number
US08354454B2

Reaction notes

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