HCID 19993541, compound → HCID 19993498, compound

HRID 345067Notes

Reaction equation

HRID 345067 reaction equation
[Si:1]([O:8][CH:9]([CH2:21][O:22][Si](C(C)(C)C)(C)C)[CH2:10][O:11][CH2:12][P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(O)(=O)C>[Si:1]([O:8][CH:9]([CH2:21][OH:22])[CH2:10][O:11][CH2:12][P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 19993541HCID 19993541, compound

Product 1

HCID 19993498HCID 19993498, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of diethyl 2,3-bis(t-butyldimethylsilyloxy)propoxymethylphosphonate (1 g, 2.13 mmol) in 80% aqueous acetic acid (20 ml) was stirred at 20° C. for 4 h. The solvent was evaporated in vacuo, co-evaporated with toluene and the residue chromatographed on silica, eluting with ethyl acetate-hexane 2:1, affording diethyl 2-t-butyldimethylsilyloxy-3-hydroxypropoxymethylphosphonate (340mg, 45%) as a clear liquid. νmax (film) 3400, 1460, 1390 and 1250 cm-1 ; δH (CDCl3), 0.05 (6H, s, CH3SiCH3), 0.83 (9H, s, (CH3)3CSi), 1.25 (6H, t, J6.9 Hz, 2×CH3CH2), 2.16 (1H, br.s, D2O exchangeable, OH), 3.50 (4H, m, CH2OH+CH2OCH2P), 3.72 (3H, m, CHOSi+CH2P), 4.05 (4H, m, 2×CH3CH2); m/z (FAB+ve Ion), 357 (MH+).

Workup

  1. customThe solvent was evaporated in vacuo, co-evaporated with toluene
  2. customthe residue chromatographed on silica
  3. washeluting with ethyl acetate-hexane 2:1

Sources & evidence

ORD record
ord-19456756e17444a6aea48cb02faedf7b
Source dataset
uspto-grants-1991_10
Patent number
US05055458

Reaction notes

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