Water → 1-(1,3-Benzodioxol-5-yl)cyclobutanecarboxylic Acid
Reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11]#N)=[CH:4][C:3]=2[O:2]1.Br[CH2:14][CH2:15][CH2:16]Br.[H-].[Na+].[OH-:20].[K+].[OH2:22]>C(O)CO>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([C:10]3([C:11]([OH:22])=[O:20])[CH2:16][CH2:15][CH2:14]3)=[CH:4][C:3]=2[O:2]1Participants
Procedure
The title compound was prepared in an analogous manner to that in Example 9 from 3,4-methylenedioxyphenylacetonitrile and 1,3-dibromopropane. 2.1 eq of NaH and 1.1 eq of 1,3-dibromopropane were used. The mixture of 3,4-methylenedioxyphenylacetonitrile and 1,3-dibromopropane was added at 0° C. The afforded 1-(3,4-methylenedioxyphenyl)cyclobutanecarbonitrile was purified by chromatography on silica gel using petroleum ether-EtOAc 94:6 as eluent. The product (11 mmol) was then refluxed with KOH (33 mmol) in ethyleneglycol (16.6 mL) and H2O (1.4 mL) for 7 h. The cooled mixture was extracted with Et2O. The aqueous layer was acidified and extracted with Et2O. The crude was chromatographed on silica gel using EtOAc-HOAc 99:1 as eluent to give the desired product. The yield was 1.1 g (26%); 1H NMR (CDCl3) δ 1.80-1.95 (m, 1H), 1.97-2.12 (m, 1H), 2.40-2.50 (m, 2H), 2.75-2.85 (m, 2H), 5.91 (s, 2H), 6.75-6.80 (m, 3H).
Workup
- additionwas added at 0° C
- customThe afforded 1-(3,4-methylenedioxyphenyl)cyclobutanecarbonitrile was purified by chromatography on silica gel
- extractionThe cooled mixture was extracted with Et2O
- extractionextracted with Et2O
- customThe crude was chromatographed on silica gel
Sources & evidence
- ORD record
- ord-25efa57780fa4fedac56073cf16a1b08
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06124354
Reaction notes
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