Pyridine → HCID 70407612, compound

HRID 414769Notes

Reaction equation

HRID 414769 reaction equation
[P:1]([O-:32])([O:28][CH2:29][CH2:30]Br)([O:3][C@@H:4]1[CH2:9][CH2:8][CH2:7][O:6][C@H:5]1[CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:2].[N:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[P:1]([O-:32])([O:28][CH2:29][CH2:30][N+:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([O:3][C@@H:4]1[CH2:9][CH2:8][CH2:7][O:6][C@H:5]1[CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:2]

Participants

3

Reactant 2

HCID 1049PyridineHCID 86742640HCID 86742640, compound

Product 1

HCID 70407612HCID 70407612, compound

Conditions

Temperature
80 °C

Procedure

1.512 g of dl-trans-2-hexadecyloxymethyltetrahydropyran-3-yl 2-bromoethyl phosphate (prepared as described in the first half of Example 1) was dissolved in 20 ml of pyridine, and the resulting solution was heated, with stirring, at 80° C. for 20 hours. The mixture was then cooled and the pyridine was removed by distillation under reduced pressure. The residue was subjected to column chromatography through 45 g of silica gel. The fraction eluted with a 60:35:5 by volume mixture of methylene chloride, methanol and water gave 1.422 g of the title compound as a white powder, melting at 123°-129° C.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureThe mixture was then cooled
  3. customthe pyridine was removed by distillation under reduced pressure
  4. washThe fraction eluted with a 60:35:5 by volume mixture of methylene chloride, methanol and water

Sources & evidence

ORD record
ord-7754f75942ce432692cb1802360da689
Source dataset
uspto-grants-1988_12
Patent number
US04794183

Reaction notes

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