4-Methoxyphenol → HCID 10221421, compound
Reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:32][CH2:33][CH2:34][C:35]1[CH:43]=[CH:42][CH:41]=[C:40]2[C:36]=1[CH2:37][C:38](=[O:44])[NH:39]2.[CH3:45][O:46][C:47]1[CH:52]=[CH:51][C:50](O)=[CH:49][CH:48]=1>O1CCCC1>[CH3:45][O:46][C:47]1[CH:52]=[CH:51][C:50]([O:32][CH2:33][CH2:34][C:35]2[CH:43]=[CH:42][CH:41]=[C:40]3[C:36]=2[CH2:37][C:38](=[O:44])[NH:39]3)=[CH:49][CH:48]=1Participants
Procedure
Diethyl azodicarboxylate (0.47 mL, 3 mmol) was added to a solution of triphenylphosphine (0.786 g, 3 mmol) in tetrahydrofuran (10 mL) under nitrogen atmosphere. The mixture was stirred for 15 minutes. To it was then added 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (0.53 g, 3 mmol) followed by 4-methoxyphenol (0.372 g, 3 mmol). The mixture was stirred at room temperature for 18 hours and the solvent was evaporated. The residue was dissolved in ethyl acetate (150 mL) and the organic solvent was washed with 2 N hydrochloric acid (3×30 mL), saturated sodium bicarbonate solution and brine. The residue was chromatographed on silica gel eluting with ethyl acetate:hexane 2:8 to give 0.14 g (16%) 4-[2-(4-Methoxy-phenoxy)-ethyl]-1,3-dihydro-indol-2-one.
Workup
- stirringThe mixture was stirred at room temperature for 18 hours
- customthe solvent was evaporated
- dissolutionThe residue was dissolved in ethyl acetate (150 mL)
- washthe organic solvent was washed with 2 N hydrochloric acid (3×30 mL), saturated sodium bicarbonate solution and brine
- customThe residue was chromatographed on silica gel eluting with ethyl acetate:hexane 2:8
Sources & evidence
- ORD record
- ord-ebcb7fd933924308babeeb4146fe3c8f
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06689806B1
Reaction notes
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