Triethylamine → Diethyl (t-Butyldimethylsiloxy)methylphosphonate

HRID 2379540Notes

Reaction equation

HRID 2379540 reaction equation
[OH:1][CH2:2][P:3](=[O:10])([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6].C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]>ClCCl.O>[O:1]([CH2:2][P:3](=[O:10])([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6])[Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 76513Diethyl phosphonomethanol

Product 1

HCID 12606850Diethyl (t-Butyldimethylsiloxy)methylphosphonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of diethyl hydroxylmethylphosphonate (2.13 g, 12.7 mmol), triethylamine (2.12 ml, 15.2 mmol) and dimethylaminopyridine (77 mg, 0.63 mmol) in dichlormethane at 0° C. under argon, at r.t., was added t-butyldimethylsilyl chloride (1.85 g, 12.8 mmol) in dichloromethane (5 ml). After 14 hr the resulting slurry was poured into water (100 ml) and extracted with dichloromethane (2×100 ml). The organic extracts were dried (Na2SO4), concentrated in vacuo and the resulting oil chromatographed on silica gel eluted with ethylacetate:hexanes (1:1, v:v) to afford the title compound as a clear oil.

Workup

  1. extractionextracted with dichloromethane (2×100 ml)
  2. dry with materialThe organic extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customthe resulting oil chromatographed on silica gel
  5. washeluted with ethylacetate:hexanes (1:1, v:v)

Sources & evidence

ORD record
ord-257fbb3faf53435391ee767d45efb057
Source dataset
uspto-grants-1994_11
Patent number
US05362906

Reaction notes

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