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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1766930Generated: October 26, 2026

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

https://huagongshe.com/reaction/1766930

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantEthyl AcetateHCID 8857—
ReactantTetrabutylammonium FluorideHCID 2724141—
ReactantDiallyl 2-[(tert-butyldimethylsilyl)oxymethyl]-6-chlorobenzyl phosphateHCID 21110492—
SolventTetrahydrofuranHCID 8028—
SolventHexaneHCID 8058—
ProductDiallyl 2-chloro-6-(hydroxymethyl)benzyl phosphateHCID 1786256383%

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07230023B2
Source datasetuspto-grants-2007_06
ORD IDord-7b02223420fd4a368ea6ac2e0157d8bf
Source noteuspto-grants-2007_06