Water → Diallyl 2-(hydroxymethyl)-6-methylbenzyl phosphate

HRID 1766917Notes

Reaction equation

HRID 1766917 reaction equation
[P:1]([O:11][CH2:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:20][O:21][Si](C(C)(C)C)(C)C)([O:7][CH2:8][CH:9]=[CH2:10])([O:3][CH2:4][CH:5]=[CH2:6])=[O:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>O1CCCC1.CCCCCC>[P:1]([O:11][CH2:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:20][OH:21])([O:7][CH2:8][CH:9]=[CH2:10])([O:3][CH2:4][CH:5]=[CH2:6])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 21110494Diallyl 2-[(tert-butyldimethylsilyl)oxymethyl]-6-methylbenzyl phosphate

Product 1

HCID 17862639Diallyl 2-(hydroxymethyl)-6-methylbenzyl phosphateYield 87.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of diallyl 2-[(tert-butyldimethylsilyl)oxymethyl]-6-methylbenzyl phosphate (6.02 g, 14.1 mmol) obtained from Example 22-(3) in tetrahydrofuran (50 ml) was added tetrabutylammonium fluoride (1 mol/l tetrahydrofuran solution; 17.6 ml, 17.6 mmol), and the mixture was stirred at room temperature for 3 hours. Water was added thereto, and the product was extracted with ethyl acetate. The solvent was distilled off under reduced pressure to give an oily residue. The residue was subjected to chromatography on a silica gel (75 g) column (eluent; ethyl acetate:hexane=3:1) to afford the title compound (3.84 g, 87% yield) as a colorless oil.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. distillationThe solvent was distilled off under reduced pressure
  3. customto give an oily residue

Sources & evidence

ORD record
ord-c8f2f668fd2b41b7a7cc1a6346687038
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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