Triethylamine → 4(2-Oxo-1,3,2-dioxaphospholane-2-yloxy)-1(4'-vinylbenyloxy)butane
Reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[CH2:15])=[CH:10][CH:9]=1.C(N(CC)CC)C.Cl[P:24]1(=[O:29])[O:28][CH2:27][CH2:26][O:25]1>C(OCC)C>[O:29]=[P:24]1([O:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]=[CH2:15])=[CH:10][CH:9]=2)[O:28][CH2:27][CH2:26][O:25]1Participants
Procedure
4-Hydroxy-1(4′-vinylbenzyloxy)butane (5) (10.03 g; 48.69 mmol) and dried triethylamine (4.92 g, 48.69 mmol) were dissolved in dry diethyl ether (150 ml) and the resulting solution placed in a rigorously dried flask. The solution was cooled to -−30° and 2-chloro-2-oxo-1,3,2-dioxaphospholane (6.94 g; 48.69 mmol) added dropwise over 30 minutes, the temperature being held at −30°. The reaction mixture was then stirred for a further 2 hours, during which time the temperature was allowed to rise to 10°. The mixture was filtered and the precipitate washed with dry ether. The filtrate was evaporated (20°/21 mm) to give a cloudy oil. The residue was shaken with 50 ml of dry ether and refiltered. Evaporation of the filtrate gave the product as a viscous yellow oil (13.73 g; 90.4%).
Workup
- additionadded dropwise over 30 minutes
- custombeing held at −30°
- customto rise to 10°
- filtrationThe mixture was filtered
- washthe precipitate washed with dry ether
- customThe filtrate was evaporated (20°/21 mm)
- customto give a cloudy oil
- customEvaporation of the filtrate
Sources & evidence
- ORD record
- ord-f32658a69b2e4cf5b03b9eb9edacff09
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06420453B1
Reaction notes
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