Triethylamine → HCID 19993500, compound

HRID 345062Notes

Reaction equation

HRID 345062 reaction equation
[OH:1][CH:2]([CH2:14][OH:15])[CH2:3][O:4][CH2:5][P:6](=[O:13])([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9].C(N(CC)CC)C.[C:23]([Si:27]([CH3:30])([CH3:29])Cl)([CH3:26])([CH3:25])[CH3:24]>CN(C)C1C=CN=CC=1.ClCCl>[Si:27]([O:15][CH2:14][CH:2]([OH:1])[CH2:3][O:4][CH2:5][P:6](=[O:13])([O:7][CH2:8][CH3:9])[O:10][CH2:11][CH3:12])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:30])[CH3:29]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 54505728HCID 54505728, compound

Product 1

HCID 19993500HCID 19993500, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl 2,3-dihydroxypropoxymethylphosphonate (4.15 g, 17.lmmol), triethylamine (1.9 g, 2.62 ml, 18.81 mmol), 4-dimethylaminopyridine (84mg, 0.7 mmol) and t-butyldimethylchlorosilane (2.92 g, 19.4 mmol) in dichloromethane (50 ml) was stirred for 16 hours at 20° C. under nitrogen. The solution was washed with water (50 ml), saturated ammonium chloride (50 ml) and dried (Na2SO4). The solvents was evaporated to leave a yellow oil which was chromatographed on silica eluting with ethyl acetate affording diethyl 3-t-butyldimethylsilyloxy-2-hydroxypropoxymethylphosphonate (4.35 g, 71%) as a pale lemon liquid. νmax (film) 3400, 1460 , 1240, 1100, 1020 and 960 cm-1 ; δH (CDCl3) 0.05(6H, s, (CH3)2Si), 0.86(9H, s,(CH3)3C), 1.31(6H, t, J7.3 Hz, 2×CH2CH3), 2.50 (1H, br.s, D2O exchangeable, OH), 3.70(7H, m, CH2OSi+CHOH+CH2OCH2P), 4.12(4H, m, 2×CH2CH3); m/z 357(MH+,3%), 341 (M-CH3+,4%); Found: C,46.89; H,9.23%; C14H33O6PSi requires C,47 17; H,9.33%

Workup

  1. washThe solution was washed with water (50 ml), saturated ammonium chloride (50 ml)
  2. dry with materialdried (Na2SO4)
  3. customThe solvents was evaporated
  4. customto leave a yellow oil which
  5. customwas chromatographed on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-40823a6c7553444697da6e14fc73b0bb
Source dataset
uspto-grants-1991_10
Patent number
US05055458

Reaction notes

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