Ethyl phenylacetate → HCID 10752615, compound
Reaction equation
[C:1]1([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].CC([N-]C(C)C)C.F[B-](F)(F)F.C1(C([N+:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:1]1([CH:7]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][N:45]=2)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
Ethyl phenylacetate (3.13 g, 19 mmol, 1.0 equiv) was added in a dropwise manner to a solution of LDA (19 mmol, 1 equiv) in THF (30 mL) at −78° C. The resultant solution was maintained at to −78° C. for 25 minutes, and then warmed to 0° C. for 10 minutes. Triphenylmethylpyridinium tetrafluoroborate (7.8 g, 19 mmol, 1.0 equiv) was added in one portion. The reaction mixture was allowed to warm to 23° C. overnight and then concentrated. The residue was partitioned between saturated aqueous ammonium chloride (50 mL) and ethyl acetate (50 mL). The layers were separated, and the aqueous layer was dried over magnesium sulfate and concentrated. The residue was purified by flash column chromatography (25% THF/hexanes) to afford ethyl α-phenylpyridylacetate (2.0 g).
Workup
- temperatureto warm to 23° C. overnight
- concentrationconcentrated
- customThe residue was partitioned between saturated aqueous ammonium chloride (50 mL) and ethyl acetate (50 mL)
- customThe layers were separated
- dry with materialthe aqueous layer was dried over magnesium sulfate
- concentrationconcentrated
- customThe residue was purified by flash column chromatography (25% THF/hexanes)
Sources & evidence
- ORD record
- ord-471fa1d961fb4a26b588a39e6273582f
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06407120B1
Reaction notes
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