Phosphate → HCID 54552717, compound
Reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].P([O-])([O-])([O-])=O>C1COCC1>[O:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH:15]1[O:14][CH:13]=[CH:12][CH2:11][CH2:10][CH2:9][OH:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of 105 (900 mg, 3 mmol) in THF (20 mL) was treated with Bu4NF (1 M in THF, 3 mL, 3 mmol, 1 equiv) at 0° C. The reaction mixture was stirred at 0° C. for 1 h and at 25° C. for 2 h. Phosphate buffer (100 mL, pH 7) was added and the mixture was extracted with EtOAc-hexane (2:1, 3×30 mL). The combined organic phase was dried (Na2SO4) and the solvent removed under vacuum. Chromatography (SiO2, 4×25 cm, 30% EtOAc-hexane containing 2% Et3N) afforded 106 (445 mg, 557 mg theoretical, 80%) as a colorless oil as a mixture of E- and Z-olefin isomers (50:50). Careful rechromatography of this material (SiO2, 4×25 cm, 10-30% EtOAc-hexane containing 2% Et3N gradient elution) enabled the partial separation of the two isomers.
Workup
- extractionthe mixture was extracted with EtOAc-hexane (2:1, 3×30 mL)
- dry with materialThe combined organic phase was dried (Na2SO4)
- customthe solvent removed under vacuum
Sources & evidence
- ORD record
- ord-e26dc81db10e4df18dc70c9202761cbe
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06281354B1
Reaction notes
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