Methyl chloroacetate → Methyl 2-chloro-3-hydroxy-3-(p-methoxyphenyl)propionate
Reaction equation
[CH:1](=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Cl:11][CH2:12][C:13]([O:15][CH3:16])=[O:14].C([N-]C(C)C)(C)C.[Li+]>O1CCCC1>[Cl:11][CH:12]([CH:1]([OH:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)[C:13]([O:15][CH3:16])=[O:14]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Condensation reaction between p-anisaldehyde and methyl chloroacetate was effected in tetrahydrofuran at -78° C. in the presence of lithium diisopropylamide, and the methyl 2-chloro-3-hydroxy-3-(p-methoxyphenyl)propionate obtained was separated into anti isomer (a mixture of (2R, 3R) isomer and (2S, 3S) isomer) and syn isomer (a mixture of (2R, 3S) isomer and (2S, 3R) isomer) by silica gel chromatography (solvent: n-hexane/ethyl acetate=3/1). NMR of these isomers was measured to determine anti isomer and syn isomer. When these isomers were analyzed by high performance liquid chromatography by use of a chiralcel OJ 4.6 mmφ×250 mm manufactured by Dicel Chemical Industries, LTD. (mobile phase: n-hexane/i-propanol=7/3, flow rate: 1.0 ml/min, column temperature: 40° C.), a retention time of the anti isomer was 9.2 minutes and 9.9 minutes, and a retention time of the syn isomer was 11.7 minutes and 13.9 minutes.
Sources & evidence
- ORD record
- ord-e2f2c5f863754b8c824013e044b908e5
- Source dataset
- uspto-grants-1993_04
- Patent number
- US05204248
Reaction notes
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