Bromotrimethylsilane → 1-Octadecyloxycarbonylphosphonic acid

HRID 2119774Notes

Reaction equation

HRID 2119774 reaction equation
[Si](Br)(C)(C)C.[CH2:6]([O:24][C:25]([P:27](=[O:32])([O:30]C)[O:28]C)=[O:26])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>C(Cl)Cl>[CH2:6]([O:24][C:25]([P:27](=[O:28])([OH:32])[OH:30])=[O:26])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 10740114Dimethyl octadecyloxycarbonylphosphonate

Product 1

HCID 107622161-Octadecyloxycarbonylphosphonic acidYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Me3SiBr (0.812 mL, 6.15 mmol) was added to a solution of dimethyl octadecyloxycarbonylphosphonate (1.0 g, 2.46 mmol) in CH2Cl2 (20 mL) under argon, and the yellow solution was stirred at room temperature for 4 hours and evaporated under reduced pressure. Trituration of the oily residue with hexane, followed by filtration and drying afforded a hygroscopic white solid of the title compound (0.757 g, 81%); mp 81-82° C.; IR (KBr): υ 2960, 2920, 2860, 1730, 1720, 1475, 1465, 1265, 1240, 1225 cm−1; 1H NMR (CDCl3+CD3OD) δ0.8-1.8 (m, 35H, CH3 (CH2)16), 4.25 (t, 2H, OCH2). Anal. Calcd. for C19H39O5P.0.3H2O : C, 59.43; H, 10.42; P, 8.07. Found: C, 59.77; H, 10.91; P, 8.21.

Workup

  1. customevaporated under reduced pressure
  2. filtrationTrituration of the oily residue with hexane, followed by filtration
  3. customdrying

Sources & evidence

ORD record
ord-6b05139044a14a0d8e4412904f60cf39
Source dataset
uspto-grants-2004_02
Patent number
US06686462B2

Reaction notes

Loading…