Diethyl Ether → Diethyl (3-hydroxypropyl)phosphonate

HRID 853644Notes

Reaction equation

HRID 853644 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][CH2:10]OCC)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[BH4-].[Li+].C[CH2:17][O:18]CC>C1COCC1>[CH2:6]([O:5][P:4]([CH2:9][CH2:10][CH2:17][OH:18])(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 199879Phosphonic acid, (2-ethoxyethyl)-, diethyl esterHCID 4148881Lithium borohydride

Product 1

HCID 12594218Diethyl (3-hydroxypropyl)phosphonateYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2-ethoxy-ethyl)-phosphonic acid diethyl ester (0.500 g, 2.1 mmol) in ether (8.5 mL) and THF (1.5 mL) was treated with lithium borohydride. The reaction mixture stirred at room temperature for 1 hour and was then concentrated in vacuo. The crude mixture was partitioned between dichloromethane and water. The organic phase was washed with saturated NaHCO3 and brine, dried (MgSO4), then concentrated in vacuo. The residue was purified by silica gel chromatography (5/95—methanol/dichloromethane) to afford (3-hydroxy-propyl)-phosphonic acid diethyl ester 178 (0.100 g, 24%) as an oil: 1H NMR (CDCl3) δ 4.1 (m, 4H), 3.7 (m, 2H), 2.95 (bs, 1H), 1.85 (m, 4H), 1.30 (t, 3H); 31P NMR (CDCl3) δ 33.26; MS: 197 (M+1).

Workup

  1. concentrationwas then concentrated in vacuo
  2. customThe crude mixture was partitioned between dichloromethane and water
  3. washThe organic phase was washed with saturated NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (5/95—methanol/dichloromethane)

Sources & evidence

ORD record
ord-026f3bd07c314e0289c7af2d701ce1da
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

Loading…