Sodium Hydroxide → HCID 86593994, compound

HRID 853643Notes

Reaction equation

HRID 853643 reaction equation
[CH2:1]([O:8][P:9]([CH2:19][CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:18])[O:10]CC1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.O>[CH2:1]([O:8][P:9]([CH2:19][CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:10])[OH:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 71385663Dibenzyl [2-(benzyloxy)ethyl]phosphonate

Product 1

HCID 86593994HCID 86593994, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-benzyloxy-ethyl)-phosphonic acid dibenzyl ester (0.200 g, 0.543 mmol) in THF was added a solution of NaOH (1.36 mL, 1M) in water. The reaction mixture was stirred at room temperature for 3 hours. Most of THF was removed in vacuo and the residue was dissolved in water. The aqueous solution was washed with ethylacetate three times then acidified with 1N HCl (to pH=1) then extracted with ethylacetate. The organic phase was dried (MgSO4), concentrated and co-evaporated with toluene in vacuo to afford the mono-acid, (2-benzyloxy-ethyl)-phosphonic acid monobenzyl ester, 173 (0.160 g. 100%) as an oil with no further purification: 1H NMR (CDCl3) δ 9.25 (bs, 1H), 7.4-7.1 (m, 10H), 4.5 (s, 2H), 3.8 (m, 2H), 2.25 (m, 2H); 31P NMR (CDCl3) δ 28.63.

Workup

  1. customMost of THF was removed in vacuo
  2. dissolutionthe residue was dissolved in water
  3. washThe aqueous solution was washed with ethylacetate three times
  4. extractionthen extracted with ethylacetate
  5. dry with materialThe organic phase was dried (MgSO4)
  6. concentrationconcentrated and co-evaporated with toluene in vacuo

Sources & evidence

ORD record
ord-cf04dda331b5473490d94dfa89d4b9f8
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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