Tetrahydrofuran → HCID 86620233, compound
Reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[P:12](Cl)([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])=[O:13].[CH2:21]1[CH2:25][O:24][CH2:23][CH2:22]1>>[CH2:15]([O:14][P:12]([C:4]1[CH:6]=[C:7]([CH2:8][C:9]2[CH:6]=[CH:7][C:8]([CH2:9][CH3:10])=[CH:11][CH:10]=2)[CH:1]=[CH:2][C:3]=1[O:24][CH2:23][C:22]1[CH:21]=[CH:25][CH:3]=[CH:2][CH:1]=1)(=[O:13])[O:17][CH2:18][CH3:19])[CH3:16]Participants
Procedure
To a solution a solution of [2-benzyloxy]-5-(4-ethylbenzyl)bromobenzene (5.00 g) in THF (36.5 mL) was added 2.44 M n-butyllithium/n-hexane solution (6.5 mL) at −78° C. and the reaction mixture was stirred for 1 hr at the same temperature. A solution of diethyl chlorophosphate (2.3 mL) in THF (5.6 mL) was added to the reaction mixture at −78° C. and the reaction mixture was stirred for 1 hr at −78° C. The reaction was quenched by the addition of saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate/n-hexane) to give title compound (5.40 g) as a colorless oil.
Workup
- stirringthe reaction mixture was stirred for 1 hr at −78° C
- customThe reaction was quenched by the addition of saturated aqueous ammonium chloride
- extractionextracted with ethyl acetate
- washThe combined ethyl acetate extracts were washed with brine
- dry with materialdried over anhydrous sodium sulfate
- customevaporated
- customThe residue was purified by silica gel column chromatography (ethyl acetate/n-hexane)
Sources & evidence
- ORD record
- ord-6daab292a41f4b89bf9bfa5f0e49ba02
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691898B2
Reaction notes
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