Water → HCID 68824702, compound
Reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[O:7]1[CH2:12][CH2:11]C(=O)[CH2:9][CH2:8]1.[OH2:14].[O:15]1CC[CH2:17][CH2:16]1>>[CH2:16]([O:15][C:1](=[O:14])[C:2](=[C:5]1[CH2:9][CH2:8][O:7][CH2:12][CH2:11]1)[CH3:3])[CH3:17]Participants
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 12.9 g (54.1 mmol) of 2-phosphonopropionic acid triethyl etser in tetrahydrofuran (60 mL) was added, at 25° C. under an atmosphere of argon, 5.52 g (49.2 mmol) of potassium t-butoxide, and stirred for 10 minutes. Into this solution, 5.42 g (54.1 mmol) of tetrahydropyran-4-one was dropped and stirred for 5 hours at about 70° C. The obtained mixture was cooled to room temperature, poured into water and extracted with ether. The ether extract was washed with water (twice) and saturated brine successively, dried over anhydrous magnesium sulfate, and then, the solvent was removed. The obtained residue was purified by medium pressure liquid column chromatography on silica gel (developing solvent; hexane-ethyl acetate) to obtain 4.2 g (yield 42.1%) of 2-(tetrahydropyran-4-ylidene)propionic acid ethyl ester as colorless liquid. Its physical property is shown below.
Workup
- temperatureThe obtained mixture was cooled to room temperature
- extractionextracted with ether
- extractionThe ether extract
- washwas washed with water (twice) and saturated brine successively
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was removed
- customThe obtained residue was purified by medium pressure liquid column chromatography on silica gel (developing solvent; hexane-ethyl acetate)
Sources & evidence
- ORD record
- ord-351862a70b1548c38f668489ed5b4048
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07511144B2
Reaction notes
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