1-Hexadecene → (Z)-2-(Heptadec-2-en-1-yl)isoindoline-1,3-dione

HRID 1909503Notes

Reaction equation

HRID 1909503 reaction equation
[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:14])[CH:2]=[CH2:3].[CH2:15]=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]CC>>[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:14])/[CH:2]=[CH:3]\[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:15]

Participants

3

Reactant 2

HCID 123951-HexadeceneHCID 224401N-Allylphthalimide

Product 1

HCID 58460837(Z)-2-(Heptadec-2-en-1-yl)isoindoline-1,3-dioneYield 89.7%

Procedure

Following the allylic amide cross metathesis general procedure, 2-allylisoindoline-1,3-dione (5.50 mg, 0.0290 mmol) was treated with 1-hexadecene (63.8 mg, 0.290 mmol), 5.0 mol % of in situ-generated complex 2 (75.0 μL, 0.02 M, 1.50 i&mol; final substrate concentration=0.19 M) and allowed to stir for 1 h. The unpurified product is 85% Z (as determined by 400 MHz 1H NMR analysis). The resulting brown oil was purified by silica gel chromatography (96:2:2 hexanes:EtOAc:CH2Cl2) to afford 19g (9.80 mg, 0.0260 mmol, 87.0% yield, 85% Z isomer) as a white, crystalline solid. M.P. 56-60° C.; IR (neat): 2954(w), 2916 (s), 2849 (m), 1771 (w), 1698 (s), 1614 (w), 1464 (m), 1429 (m), 1400 (m), 1356 (w), 1335 (w), 1294 (w), 1189 (w), 1173 (w), 1155 (w), 1089 (w), 1071 (w), 1052 (w), 1024 (w), 962 (m), 930 (m); 1H NMR (400 MHz, CDCl3): 7.84 (2H, dd, J=5.4, 3.0 Hz), 7.70 (2H, dd, J=5.4, 3.0 Hz), 5.78-5.7 1 (1H, m), 5.54-5.44 (1H, m), 4.23 (2H, dd, J=6.2, 0.8 Hz), [diagnostic E isomer signal: 4.22 (1H, d, J=8 Hz)], 1.99 (2H, dd, J=13.6, 6.8 Hz), 1.43-1.19 (24H, m), 0.88 (3H, t, J=6.8 Hz); 13C NMR (100 MHz, CDCl3): 168.2, 135.6, 134.0, 132.4, 123.4, 123.3, 123.1, 77.4, 39.8, 32.3, 32.1, 29.9, 29.8, 29.8, 29.7, 29.7, 29.6, 29.6,−29.5, 29.3, 29.0,22.8, 14.3; HRMS (ESI+) [M+H]+ calcd for C25H38NO2: 384.2903, found: 384.2905.

Workup

  1. customThe resulting brown oil was purified by silica gel chromatography (96:2:2 hexanes:EtOAc:CH2Cl2)

Sources & evidence

ORD record
ord-8fdb6223a0ea43888d8d18f3ce244e86
Source dataset
uspto-grants-2013_12
Patent number
US08598400B2

Reaction notes

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