Tetrabutylammonium Hydroxide → HCID 70400285, compound

HRID 868447Notes

Reaction equation

HRID 868447 reaction equation
[P:1]([O-:50])([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][N+:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([O:3][CH2:4][CH:5]([O:26]C(=O)C1C=CC=CC=1)[CH2:6][O: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][CH2:23][CH2:24][CH3:25])=[O:2].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>CO>[P:1]([O-:50])([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][N+:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)([O:3][CH2:4][CH:5]([OH:26])[CH2:6][O: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][CH2:23][CH2:24][CH3:25])=[O:2]

Participants

4

Reactant 2

HCID 2723671Tetrabutylammonium HydroxideHCID 21288420HCID 21288420, compound

Product 1

HCID 70400285HCID 70400285, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.76 g (2.45 mmole) of 2-benzoyloxy derivative synthesized in Example 30 was dissolved in 5 ml of methanol and an aqueous solution containing 11.2 g (4.90 mmole) of 10% tetrabutylammonium hydroxide was added thereto. The mixture was stirred at room temperature for 2 hours and then subjected to the coupled two columns, one containing 40 ml of Amberlite IR-410 and the other 20 ml of Amberlite IR-120 and eluted with 95% hydrous tetrahydrofuran. The eluate was concentrated to dryness and the residue was subjected to column chromatography on 25 g of silica gel. A mixture of chloroform-methanol-water (65:25:4) was used for elution. The desired fraction was concentrated under reduced pressure to give 1.13 g (yield: 75%) of 2-(hydroxy)-3-(octadecyloxy)propyl 8-pyridiniooctyl phosphate as colorless solid.

Workup

  1. additionwas added
  2. washthe other 20 ml of Amberlite IR-120 and eluted with 95% hydrous tetrahydrofuran
  3. concentrationThe eluate was concentrated to dryness
  4. additionA mixture of chloroform-methanol-water (65:25:4)
  5. washwas used for elution
  6. concentrationThe desired fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-95012d42c2a546d9bba4beeb4043e2ca
Source dataset
uspto-grants-1988_10
Patent number
US04778912

Reaction notes

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