Phthalimide → N-(3-Butynyl)phthalimide
Reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:34]([OH:38])[CH2:35][C:36]#[CH:37].[C:39]1(=O)[NH:43][C:42](=[O:44])[C:41]2=[CH:45][CH:46]=[CH:47][CH:48]=[C:40]12>C1(C)C=CC=CC=1>[CH2:39]([N:43]1[C:34](=[O:38])[C:35]2[C:41](=[CH:45][CH:46]=[CH:37][CH:36]=2)[C:42]1=[O:44])[CH2:40][C:48]#[CH:47]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -5 °C
Procedure
Diisopropyl azodicarboxylate (316 g, 1.56 mol) was added to a solution of triphenylphosphine (PPh3) (393 g, 1.50 mol), 3-butyn-1-ol (105 g, 1.50 mol) and phthalimide (200 g, 1.36 mol) in toluene (1600 mL) which was pre-cooled with a −5° C. cooling bath at such a rate that temperature of the reaction mixture was kept between 15-25° C. The addition time was 50 min. The cooling bath was removed after the addition was finished. The reaction mixture was allowed to warm to 15-25° C. and stirred for 1 h. Then methanol (800 mL) was added. The mixture was stirred for 30 min and then filtered. The crude product was washed with methanol and dried to give a white solid (218 g) in 80% yield 99.8% purity by area. 1H NMR (DMSO-d6): δ 7.88 (m, 4 H), 3.72 (t, 2 H, J=7.0 Hz), 2.83 (t, 1 H, J=2.7 Hz), 2.55 (m, 2 H).
Workup
- temperaturecooling bath at such a rate that temperature of the reaction mixture
- customwas kept between 15-25° C
- customThe cooling bath was removed
- additionafter the addition
- temperatureto warm to 15-25° C.
- additionThen methanol (800 mL) was added
- stirringThe mixture was stirred for 30 min
- filtrationfiltered
- washThe crude product was washed with methanol
- customdried
Sources & evidence
- ORD record
- ord-6cbf6e6103364f8995eafdebc70a7417
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07253291B2
Reaction notes
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