Dicyclohexylcarbodiimide → 4-(4-pentylbenzoyloxy)phenyl Vinyl Ketone
Reaction equation
[CH:1]([C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)=[O:4])=[CH2:2].[CH2:12]([C:17]1[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=1)[CH2:13][CH2:14][CH2:15][CH3:16].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH:1]([C:3]([C:5]1[CH:6]=[CH:7][C:8]([O:11][C:21](=[O:22])[C:20]2[CH:24]=[CH:25][C:17]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:18][CH:19]=2)=[CH:9][CH:10]=1)=[O:4])=[CH2:2]Participants
6
Procedure
A mixture of 4-hydroxyphenyl vinyl ketone (c) (1.0 g), 4-pentylbenzoic acid (1.2 g), DCC (1.9 g), DMAP (0.1 g) and methylene chloride (30 mL) was stirred at room temperature for 12 hours. The white solid precipitated was filtrated out, and the solvent was evaporated away from the filtrate. The residue was dissolved in ethyl acetate, and washed with aqueous 2 M NaOH solution and then with water. The residue was purified through column chromatography (eluent: toluene) and then through recrystallization (ethanol) to obtain 0.4 g of colorless crystals, compound (1-5-11). The NMR and MS spectra of the compound well support the structure thereof.
Workup
- customThe white solid precipitated
- filtrationwas filtrated out
- customthe solvent was evaporated away from the filtrate
- dissolutionThe residue was dissolved in ethyl acetate
- washwashed with aqueous 2 M NaOH solution
- customThe residue was purified through column chromatography (eluent: toluene)
- customthrough recrystallization (ethanol)
Sources & evidence
- ORD record
- ord-54be88a9bcdb43b5a81a0fbc08a7568d
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07357964B2
Reaction notes
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