Acetonitrile → [(5,6-Dichloro-9a-ethyl-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]acetic acid
Reaction equation
[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16][CH2:17][C:18]([OH:20])=[O:19])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH3:21])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:22])[CH:5]=1.[C:23](#N)C>>[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16][CH2:17][C:18]([OH:20])=[O:19])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:21][CH3:23])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:22])[CH:5]=1Participants
Procedure
This residual partially resolved [(5,6-dichloro-9a-methyl-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]acetic acid (2.86 gm., 0.0118 mole) is treated with 1(-)cinchonidine (3.47 gm., 0.0118 mole) and the mixture dissolved in the minimum quantity of acetonitrile. After cooling for 48 hours, the salt that separates is removed by filtration and recrystallized twice from the minimum volume of acetonitrile. The pure salt is suspended in water (50 ml), treated with 6 normal hydrochloric acid (5 ml) and the precipitate that separates is removed by filtration and dried. This solid is recrystallized from a miture of tetrahydrofuran and ethyl ether to give the (-) enantiomer of [(5,6-dichloro-9a-ethyl-3-oxo-1,2,9,9a-tetrahydro-3H-fluoren-7-yl)oxy]acetic acid, m.p. 239°-241° C.,
Workup
- temperatureAfter cooling for 48 hours
- customthe salt that separates is removed by filtration
- customrecrystallized twice from the minimum volume of acetonitrile
- additiontreated with 6 normal hydrochloric acid (5 ml)
- customthe precipitate that separates is removed by filtration
- customdried
- customThis solid is recrystallized from a miture of tetrahydrofuran and ethyl ether
Sources & evidence
- ORD record
- ord-227e8b6113a94de6a342a0efa8bbad51
- Source dataset
- uspto-grants-1982_10
- Patent number
- US04356314
Reaction notes
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