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

HRID 1766910Notes

Reaction equation

HRID 1766910 reaction equation
[P:1]([O:11][CH2:12][C:13]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:21][O:22][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]([O:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:21][OH:22])([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 21110493Diallyl 2-[(tert-butyldimethylsilyl)oxymethyl]-6-methoxybenzyl phosphate

Product 1

HCID 17862616Diallyl 2-(hydroxymethyl)-6-methoxybenzyl phosphateYield 93.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of diallyl 2-[(tert-butyldimethylsilyl)oxymethyl]-6-methoxybenzyl phosphate (1.03 g, 2.33 mmol) obtained from Example 21(3) in tetrahydrofuran (10 ml) was added tetrabutylammonium fluoride (1N tetrahydrofuran solution; 2.5 ml, 2.5 mmol), and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture, then the product was extracted with ethyl acetate, and the solvent was evaporated 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=3:1˜1:0) to afford the title compound (715.0 mg, 93% yield) as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-cc54ac63253e45f890819ad277d50471
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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