Water → HCID 46834506, compound

HRID 1766922Notes

Reaction equation

HRID 1766922 reaction equation
[P:1]([O:11][CH2:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[CH2:23][O:24][Si](C(C)(C)C)(C)C)[CH:16]=[CH:15][CH:14]=1)([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:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[CH2:23][OH:24])[CH:16]=[CH:15][CH:14]=1)([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 46834505HCID 46834505, compound

Product 1

HCID 46834506HCID 46834506, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of diallyl [8-[(tert-butyldimethylsilyl)oxymethyl]-1-naphthyl]methyl phosphate (5.01 g, 10.8 mmol) obtained from Example 25-(1) in tetrahydrofuran (50 ml) was added tetrabutylammonium fluoride (1 mol/l tetrahydrofuran solution; 13.5 ml, 13.5 mmol), and the mixture was stirred at room temperature for 1 hour. Water was added and the product was extracted with ethyl acetate. The organic layer was concentrated 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˜4:1) to afford the title compound (2.22 g, 59% yield) as a colorless oil.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customto give an oily residue

Sources & evidence

ORD record
ord-230eff1f3d3e4f808fc625a458dbdcc8
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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