Imidazole → Diethyl 4-(t-butyldimethylsilyloxy)-3-hydroxybutylphosphonate

HRID 373886Notes

Reaction equation

HRID 373886 reaction equation
[OH:1][CH:2]([CH2:13][OH:14])[CH2:3][CH2:4][P:5](=[O:12])([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8].N1C=CN=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>O1CCCC1.CCOCC>[Si:20]([O:14][CH2:13][CH:2]([OH:1])[CH2:3][CH2:4][P:5](=[O:12])([O:6][CH2:7][CH3:8])[O:9][CH2:10][CH3:11])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 19808663Diethyl 3,4-dihydroxybutylphosphonate

Product 1

HCID 19808612Diethyl 4-(t-butyldimethylsilyloxy)-3-hydroxybutylphosphonate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diethyl 3,4-dihydroxybutylphosphonate (8.5 g, 0.038 mol) in dry tetrahydrofuran (200 ml) was added imidazole (5.25 g, 0.077 mol). After stirring at ambient temperature for 2 minutes, t-butyldimethysilyl-chloride (5.8 g, 0.038 mol) was added. After 18 hours, the solution was filtered and the filtrate evaporated to give a colorless oil. The oil was dissolved in ether, and washed with water. The organic phase was dried (magnesium sulphate) and evaporated to give an oil which was purified by chromatography on silica gel (dichloromethane-methanol (98:2) as eluant). The title compound was obtained as an oil (8 g, 62%). IR:υmax (film), 3400, 2940, 2860, 1250, 1170, 960, 840, 780 cm-1. 1H NMR: δH (CDCl3) 0.00 (6H, s, SiMe2), 0.83 (9H, s, SiBut), 1.25 (6H, t, J=7Hz, (OCH2CH3)2), 1.5-2.0 (4H, m, CH2CH2P), 2.7 (1H, bs, D2O exchangeable, OH), 3.35-3.65 (3H, m, OCH2CH), 4.0 (4H, m, (OCH2CH3)2) Found: C, 48.66; H, 9.83%. C14H33O5SiP requires: C, 49.39; H, 9.77%.

Workup

  1. waitAfter 18 hours
  2. filtrationthe solution was filtered
  3. customthe filtrate evaporated
  4. customto give a colorless oil
  5. washwashed with water
  6. dry with materialThe organic phase was dried (magnesium sulphate)
  7. customevaporated
  8. customto give an oil which
  9. customwas purified by chromatography on silica gel (dichloromethane-methanol (98:2) as eluant)

Sources & evidence

ORD record
ord-5423b5f348d44e9f937caa0114a0c423
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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