Water → 2-Azido-1-Phenylvinyl 3-Cyclopentylpropionate
Reaction equation
[N:1]([CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6])=[N+:2]=[N-:3].[Li+].CC([N-]C(C)C)C.[CH:21]1([CH2:26][CH2:27][C:28](Cl)=[O:29])[CH2:25][CH2:24][CH2:23][CH2:22]1.O>C1COCC1>[CH:21]1([CH2:26][CH2:27][C:28]([O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:4][N:1]=[N+:2]=[N-:3])=[O:29])[CH2:25][CH2:24][CH2:23][CH2:22]1Participants
Procedure
To a stirred solution of α-azidoacetophenone (3.37 g, 20.9 mmol) in dry THF (50 mL) was added a solution of LDA (2.0 M in cyclohexane, 12.5 mL, 25 mmol) at -78° C. under nitrogen dropwise. After the reaction mixture was stirred for 1 h, a solution of 3-cyclopentylpropionyl chloride (5.04 g, 31.35 mmole, 1.5 eq.) was added to the dark red mixture, and after 10 min, the mixture was slowly warmed to room temperature. Stirring was continued for 1 h and the resultant yellow mixture was poured into water and extracted with ethyl acetate (3×50 mL). The combined organics were washed with water and brine, dried over magnesium sulfate, and filtered. Evaporation of solvent followed by column chromatography on silca gel (eluent: 2:1 ethyl acetate:hexanes) gave 4.0 g (71.5%) of the title compound: 1H NMR (400 MHz, CDCl3) ε 7.32-7.26 (m, 5H), 6.53 (s, 1H), 2.58 (t, 2H, J=7.5 Hz), 1.89-1.70 (m, 5H), 1,65-1.40 (m, 4H), 1.2 (m, 2H).
Workup
- waitafter 10 min
- stirringStirring
- waitwas continued for 1 h
- extractionextracted with ethyl acetate (3×50 mL)
- washThe combined organics were washed with water and brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customEvaporation of solvent
Sources & evidence
- ORD record
- ord-01a88e5ebb7e4fb899292f0fefb59b74
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05561142
Reaction notes
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