Acetyl chloride → HCID 10660881, compound
Reaction equation
[C:1]([C:5]1[C:10]2[O:11][CH2:12][C:13]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[C:7]([C:16](=[N:18][OH:19])[NH2:17])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:20](Cl)(=O)[CH3:21]>N1C=CC=CC=1>[C:1]([C:5]1[C:10]2[O:11][CH2:12][C:13]([CH3:14])([CH3:15])[C:9]=2[CH:8]=[C:7]([C:16]2[N:17]=[C:20]([CH3:21])[O:19][N:18]=2)[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
To a solution of 7-tert-butyl-2,3-dihydro-3,3-dimethyl-5-benzo-[b]furancarboxamide oxime (1.05 g. 4.0 mmol) in 20 mL of pyridine is added acetyl chloride (0.43 mL, 6.0 mmol). The reaction mixture is heated at 95° C. for 22 h and cooled to room temperature. Pyridine is removed in vacuo at 50° C.; the residue is partitioned between water and ethyl acetate. The organic layer is washed with water and with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give 1.33 g of the crude product. Purification by flash column chromatography on silica gel (10% ethyl acetate-hexane) produces about 0.60 g (52%) of the title compound as a colorless solid: mp 81-82° C.
Workup
- temperaturecooled to room temperature
- customPyridine is removed in vacuo at 50° C.
- customthe residue is partitioned between water and ethyl acetate
- washThe organic layer is washed with water and with brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto give 1.33 g of the crude product
- customPurification by flash column chromatography on silica gel (10% ethyl acetate-hexane)
Sources & evidence
- ORD record
- ord-ed1cdfb73d1143838dbf08c4ddafd7fc
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05981547
Reaction notes
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