Sodium hydride → HCID 86657395, compound

HRID 1805919Notes

Reaction equation

HRID 1805919 reaction equation
[P:1]([O-:18])([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H-].[Na+].Br[CH2:22][CH2:23][CH2:24][O:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][O:27]1>CN(C=O)C.O>[O:27]1[CH2:28][CH2:29][CH2:30][CH2:31][CH:26]1[O:25][CH2:24][CH2:23][CH2:22][P:1](=[O:18])([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 21904359Dibenzylphosphite

Product 1

HCID 86657395HCID 86657395, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Dibenzyl phosphite (1.70 mL, 7.63 mmol) was added to a stirred suspension of sodium hydride (60% dispersion in mineral oil) (0.381 g, 9.53 mmol) in dry DMF (11.4 mL) at 25° C. under N2. After 15 min 2-(3-bromopropoxy)tetrahydro-2H-pyran (1.29 mL, 7.63 mmol) was added and the mixture was stirred at 25° C. for 5 h. The reaction mixture was diluted with water (20 mL) and extracted with Et2O (2×40 mL). The combined organic extracts were washed with brine (20 mL), dried (Na2SO4) and concentrated in vacuo to afford dibenzyl [3-(tetrahydro-2H-pyran-2-yloxy)propyl]phosphonate. Rf=0.06 (20% EtOAc/hexanes). LCMS calc.=427.17; found=427.15 (M+Na)+.

Workup

  1. extractionextracted with Et2O (2×40 mL)
  2. washThe combined organic extracts were washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-857449edf9e746348b625e63cb6df314
Source dataset
uspto-grants-2013_01
Patent number
US08354454B2

Reaction notes

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