3-(3-(1,3-Dioxoisoindolin-2-yl)propyl)benzaldehyde → 2-(3-(3-(Pent-1-enyl)phenyl)propyl)isoindoline-1,3-dione

HRID 1967669

Reaction equation

HRID 1967669 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CCC>[CH:18]([C:17]1[CH:16]=[C:15]([CH2:14][CH2:13][CH2:12][N:3]2[C:2](=[O:1])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]2=[O:11])[CH:22]=[CH:21][CH:20]=1)=[CH:4][CH2:5][CH2:6][CH3:7]

Participants

3

Reactant 1

HCID 577664653-(3-(1,3-Dioxoisoindolin-2-yl)propyl)benzaldehyde

Product 1

HCID 689444822-(3-(3-(Pent-1-enyl)phenyl)propyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 159628Butyltriphenylphosphonium bromideCatalyst

Procedure

Coupling of aldehyde 29 with butyltriphenylphosphonium bromide following the method used in Example 1 gave 2-(3-(3-(pent-1-enyl)phenyl)propyl)isoindoline-1,3-dione as a yellow oil. Yield (0.198 g, 46%), isomer ratio 5:1: 1H NMR (500 MHz, CDCl3) δ 7.84-7.81 (m, 2H), 7.72-7.68 (m, 2H), 7.22-7.01 (m, 4H), 6.37-6.16 (m, 1H), 5.66-5.61 (m, 1H), 3.76 (t, J=7.2 Hz, 2H), 2.69-2.65 (m, 2H), 2.31-2.15 (m, 2H), 2.04 (quint, J=7.5 Hz, 2H), 1.51-1.40 (m, 2H), 0.97-0.92 (m, 3H).

Sources & evidence

ORD record
ord-91aeb1322cb3447fafadbafa23b06544
Source dataset
uspto-grants-2013_04
Patent number
US08420863B2

Linked notes

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