Water → Diallyl 2-chloro-6-(hydroxymethyl)benzyl phosphate

HRID 1766930Notes

Reaction equation

HRID 1766930 reaction equation
[P:1]([O:11][CH2:12][C:13]1[C:18]([Cl: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:14]([CH2:20][OH:21])=[CH:15][CH:16]=[CH:17][C:18]=1[Cl:19])([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 21110492Diallyl 2-[(tert-butyldimethylsilyl)oxymethyl]-6-chlorobenzyl phosphate

Product 1

HCID 17862563Diallyl 2-chloro-6-(hydroxymethyl)benzyl phosphateYield 83%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of diallyl 2-[(tert-butyldimethylsilyl)oxymethyl]-6-chlorobenzyl phosphate (4.41 g, 9.87 mmol) obtained from Example 27-(2) in tetrahydrofuran (50 ml) was added tetrabutylammonium fluoride (1N tetrahydrofuran solution; 10 ml, 10 mmol), and the mixture was stirred at room temperature for 40 minutes. Water was added to the mixture, then the product was extracted with ethyl acetate, and the solvent was distilled off under reduced pressure to give an oily residue. The residue was subjected to chromatography on a silica gel (50 g) column (eluent; ethyl acetate:hexane=1:1˜3:1) to afford the title compound (2.71 g, 83% 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-7b02223420fd4a368ea6ac2e0157d8bf
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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