Trimethyl phosphite → HCID 19028505, compound

HRID 2255838Notes

Reaction equation

HRID 2255838 reaction equation
COC1C=CC(CCCC)=CC=1CCl.[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][C:18]=1[CH2:19]Cl.[P:29]([O:34]C)([O:32][CH3:33])[O:30][CH3:31]>>[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][C:18]=1[CH2:19][P:29](=[O:34])([O:32][CH3:33])[O:30][CH3:31]

Participants

4

Reactant 3

HCID 8472Trimethyl phosphiteHCID 124144024-tert-Butyl-2-(chloromethyl)-1-methoxybenzeneHCID 19028507HCID 19028507, compound

Product 1

HCID 19028505HCID 19028505, compoundYield 55%

Procedure

A solution of 2-methoxy-5-butylbenzylchloride (10 (1.65 g, 7.76 mmol) in trimethyl phosphite (25 ml) was heated at reflux for 22 h under argon. The excess trimethyl phosphite was distilled off under reduced pressure and the residue was purified by column chromatography over silica (dichloromethane/methanol; 49:1), by distillation under reduced pressure (b.p. 215° C. at 0.075 mm Hg) and finally by column chromatography over silica (dichloromethane/methanol; 19:1) to yield a colourless oil of (11) (1.21 g, 55%); 67H (CDCl3) 1.33 (9 H, s, tert-butyl), 3.17 (2 H, d, J=21.8 Hz, CH2P), 3.64 (3 H, s, OCH3), 3.69 (3 H, s, OCH3), 3.86 (3 H, s, Ar-OCH3), 6.83 (1 H, d, J=8.6 Hz, H3), 7.08 (t H, d, J=16.4 Hz, vinylic H), 7.24, 7.29, 7.41, 7.48, and 7.50 (5 H, m, PhH and vinylic H), and 7.57 (1 H, d, J=2.4 Hz, PhH).

Workup

  1. temperatureat reflux for 22 h under argon
  2. distillationThe excess trimethyl phosphite was distilled off under reduced pressure
  3. distillationthe residue was purified by column chromatography over silica (dichloromethane/methanol; 49:1), by distillation under reduced pressure (b.p. 215° C. at 0.075 mm Hg) and finally by column chromatography over silica (dichloromethane/methanol; 19:1)

Sources & evidence

ORD record
ord-19505eef2cd84f70ae1fea9115a3aa4b
Source dataset
uspto-grants-1997_08
Patent number
US05653914

Reaction notes

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