Propionyl chloride → HCID 15156825, compound
Reaction equation
[C:1]([O:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[CH2:6])(=[O:3])[CH3:2].[CH3:13]C([O-])(C)C.[K+].C(Cl)(=O)CC>O1CCCC1>[C:1]([O:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[CH2:6])(=[O:3])[CH2:2][CH3:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 8.11 g (50 mmol) of 1-phenylvinyl acetate (prepared as described in Example 1) in 80 ml of anhydrous tetrahydrofuran was placed in a 500 ml round bottomed flask and cooled to −75°. A solution of 6.16 g (55 mmol) of potassium tert-butylate in 60 ml of anhydrous tetrahydrofuran was slowly added (40′) and the mixture was stirred for 1 h at −75°. A solution of propionyl chloride (55 mmol) in 20 ml of anhydrous tetrahydrofuran was slowly added (20′) and, after 2 h at −75°, the cooling bath was removed and 60 ml of a saturated solution of NaHCO3 was rapidly added. The temperature rose rapidly to −10° and the mixture was extracted with ether. After usual workup, the product was purified by flash chromatography (SiO2, pentane/ether 8/2), bulb-to-bulb distillation and preparative GC using a 1.2 m×6 mm column loaded with 10% SE-30 on Supelcoport® 80–100 mesh, vector gas: helium at 30 ml/min. The product was obtained in 14% yield.
Workup
- temperaturecooled to −75°
- customthe cooling bath was removed
- addition60 ml of a saturated solution of NaHCO3 was rapidly added
- customrose rapidly to −10°
- extractionthe mixture was extracted with ether
- distillationAfter usual workup, the product was purified by flash chromatography (SiO2, pentane/ether 8/2), bulb-to-bulb distillation and preparative GC
- customThe product was obtained in 14% yield
Sources & evidence
- ORD record
- ord-14a127be1d174f1fa5f3c3d99b22c6d9
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07129206B2
Reaction notes
Loading…