Acetic Acid → HCID 22250413, compound
Reaction equation
CO[C:3]([C:5]1[C:14]2[O:13][CH2:12][CH2:11][O:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[Cl:15][CH2:16]I.[Li+].CC([N-]C(C)C)C.C(O)(=O)C>C1COCC1>[Cl:15][CH2:16][C:3]([C:5]1[C:14]2[O:13][CH2:12][CH2:11][O:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a mixture of 2,3-dihydro-benzo[1,4]dioxine-5-carboxylic acid methyl ester (100 mg, 0.515 mmol) and chloroiodomethane (0.075 ml, 1.03 mmol) in 1 ml of THF was added a solution of LDA in THF (2M, 0.57 ml, 1.13 mmol) dropwise at −78° C. over 15 min. The reaction mixture was stirred at −78° C. for 10 min. A solution of acetic acid (0.75 ml) in THF (5 ml) was added dropwise over 5 min at −78° C. The resulting solution was stirred at the same temperature for additional 10 min. and was then partitioned between ethyl acetate and water. The organic layer was washed with aqueous sodium bicarbonate, brine, dried over MgSO4 and concentrated in vacuo to give the crude 2-chloro-1-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-ethanone as a light brown liquid.
Workup
- stirringThe resulting solution was stirred at the same temperature for additional 10 min.
- customwas then partitioned between ethyl acetate and water
- washThe organic layer was washed with aqueous sodium bicarbonate, brine
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-8271dbdd5e044ddf9b078c4aa691a27e
- Source dataset
- uspto-grants-2006_02
- Patent number
- US06995181B2
Reaction notes
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