HCID 11396283, compound → HCID 11324149, compound
Reaction equation
[F:1][C:2]([F:21])([C:17]([F:20])([F:19])[F:18])[CH2:3][CH:4](I)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13]>C(O)(=O)C.[Zn]>[F:1][C:2]([F:21])([C:17]([F:18])([F:19])[F:20])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
To a stirred solution of the product from step (b) (2.5 g) in acetic acid (15 ml) was added zinc dust (0.75 g) and the reaction stirred at 20° C. for 17 hours. The reaction mixture was then filtered through a celite pad. The solvent was removed from the filtrate in vacuo to leave a dark orange residue that was partitioned between ethyl acetate (20 ml) and water (20 ml). The ethyl acetate layer was washed with saturated sodium bicarbonate solution (10 ml), dried and the solvent was removed in vacuo to leave the title compound as a dark red oil (1.66 g). A 1:6 mixture of elimination by-product:product, respectively, was produced.
Workup
- filtrationThe reaction mixture was then filtered through a celite pad
- customThe solvent was removed from the filtrate in vacuo
- customto leave a dark orange residue that
- customwas partitioned between ethyl acetate (20 ml) and water (20 ml)
- washThe ethyl acetate layer was washed with saturated sodium bicarbonate solution (10 ml)
- customdried
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-88e25ed642d94617a1ecd40cf631eafa
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07195752B2
Reaction notes
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