Acetic Acid → 3-[1-(Benzyloxycarbonyl)indol-3-yl]-2-oxopropyl Acetate
Reaction equation
[C:1]([O:4]CC(=O)CC1C=CC(Cl)=C(Cl)C=1)(=[O:3])[CH3:2].[CH2:17]([O:24][C:25]([N:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]([CH2:36][C:37](=[O:40])[CH2:38]Cl)=[CH:28]1)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O)(=O)C.C(N(CC)CC)C>>[C:1]([O:4][CH2:38][C:37](=[O:40])[CH2:36][C:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:27]([C:25]([O:24][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:26])[CH:28]=1)(=[O:3])[CH3:2]Participants
5
Procedure
The procedure described above for the synthesis of 3-(3,4-dichlorophenyl)-2-oxopropyl acetate was followed, reacting 3-[1-(benzyloxycarbonyl)indol-3-yl]-1-chloropropan-2-one (19.28 g, 56.4 mmol) with acetic acid (6.5 mL, 6.8 g, 0.11 mol) and triethylamine (15.7 mL, 11.4 g, 0.113 mol). Flash chromatography over silica gel (25% ethyl acetate in hexanes) gave pure product as an orange oil that solidified under vacuum to a yellow solid (9.06 g, 44% yield): 1H NMR (400 MHz, CDCl3) δ 2.15 (s, 3H) 3.81 (d, J=0.8 Hz, 2H) 4.73 (s, 2H) 5.45 (s, 2H) 7.26-7.30 (m, 1H) 7.32-7.51 (m, 7H) 7.62 (s, 1H) 8.18 (s, 1H).
Workup
- customFlash chromatography over silica gel (25% ethyl acetate in hexanes) gave pure product as an orange oil that
Sources & evidence
- ORD record
- ord-7f7a0bc0107444688f42960cdebc61d7
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07465798B2
Reaction notes
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