Water → HCID 10608502, compound

HRID 373877Notes

Reaction equation

HRID 373877 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])(C(C)(C)C)(C)C.O>C(O)(=O)C>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][P:13](=[O:20])([O:14][CH2:15][CH3:16])[O:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 962WaterHCID 19808650HCID 19808650, compound

Product 1

HCID 10608502HCID 10608502, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

Diethyl 4-(tert-butyldimethylsilyloxy)butylphosphonate (1.7 g, 5.25 mmol) was dissolved in 80% acetic acid (5 ml) and the resulting solution was stirred at 70° C. for 20 min. The reaction mixture was then allowed to cool and water (2 ml) was added. The resulting mixture was washed with hexane (3×5 ml) and chloroform (5×5 ml). The combined chloroform phase was washed with sat. aq. NaHCO3 (2×10 ml), water (1×10 ml) and the solvents were evaporated under vacuum. The residue was chromatographed on silica gel (eluted with chloroform: ethanol 96:4) to give the title compound as a colorless oil (1 g, 91%). 1H NMR:δH ((CD3)2SO), 1.22 (6H, t, J=7Hz, (OCH2CH3)2), 1.47 (4H, br.s, CH2CH2), 1.68 (2H, m, CH2P), 3.38 (2H, br.s, HOCH 2), 3.96 (4H, m, (OCH2CH3)2), 4.43 (1H, br.s, HOCH2, D2O exchangeable).

Workup

  1. temperatureto cool
  2. washThe resulting mixture was washed with hexane (3×5 ml) and chloroform (5×5 ml)
  3. washThe combined chloroform phase was washed with sat. aq. NaHCO3 (2×10 ml), water (1×10 ml)
  4. customthe solvents were evaporated under vacuum
  5. customThe residue was chromatographed on silica gel (eluted with chloroform: ethanol 96:4)

Sources & evidence

ORD record
ord-41f329cc89e74519824625edc2feab2e
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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