Trimethylamine → HCID 54029019, compound

HRID 2255842Notes

Reaction equation

HRID 2255842 reaction equation
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH3:7][O:8][C:9]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:10]=1[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])=[CH:15][CH:14]=1.CN(C)C.CCOCC>O1CCCC1.O>[C:1]([O:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][O:19][C:16]1[CH:15]=[CH:14][C:13]([CH:12]=[CH:11][C:10]2[CH:27]=[C:28]([O:31][CH3:32])[CH:29]=[CH:30][C:9]=2[O:8][CH3:7])=[CH:18][CH:17]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

7

Reactant 4

HCID 1146TrimethylamineHCID 3283Diethyl EtherHCID 13528Methacryloyl chlorideHCID 54033643HCID 54033643, compound

Product 1

HCID 54029019HCID 54029019, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Methacryloylchloride 90%, 0.52 ml, 4.8 mmol) was added dropwise To a stirred solution of 6-(2',5'-dimethoxy-4-stilbenoxy)hexanol (14) (1.54 g, 4.32 mmol) and dry trimethylamine (0.76 ml, 5.5 mmol) in dry tetrahydrofuran (25 ml) under argon. The reaction mixture was stirred at 60° C. for 23 h. Ether (200 ml) and water (100 ml) were added. The organic layer was washed with water (3×100 ml), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography over silica (dichloromethane/hexane; 4:1 to 1:0) to yield (15) (1.48 g, 81 %] as an oil; δH (CDCl3) 1.48 (4 H, m, CH2), 1.70 (2 H, m, CH2), 1.80 (2 H, m, CH2), 1.95 (3 H, m, CH3), 3.81 (3 H, s, OCH3), 3.83 (3 H, s, OCH3), 3.96 (2 H, J=6.4 Hz, CCH2), 4.16 (2 H, t, J=6.6 Hz, OCH2), 5.55 (1 H, m, HA), 6.10 (1 H, m, HB), 6.76 (1 H, dd, JH4',H3' =8.2 Hz, JH6',H4' =2.9 Hz, H4'), 6.82 (1 H, d, JH4',H3' =8.2 Hz, H3'), 6.87 and 7.46 (4 H, AA'BB', H2, H3, H5, and H6), 7.04 (1 H, d, J=16.5 Hz,. vinytic H), 7.13 (1 H, d, JH4',H6' =2.9 Hz, H6') and 7.32 (1 H, d, J=16.4 Hz, vinylic H); δc (CDCl3) 18.3, 25.69, 25.74, 28.5, 29.1, 53.4, 55.7, 56.2, 64.6, 67.7, 111.3, 112.2, 113.1, 114.5, 120.9, 125.2, 127.5, 127.7, 128.8, 130.4, 136.4, 151.2, 153.7, 158.6 and 167.4.

Workup

  1. washThe organic layer was washed with water (3×100 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography over silica (dichloromethane/hexane; 4:1 to 1:0)

Sources & evidence

ORD record
ord-c04403719c3b4b88825c2f22a957940c
Source dataset
uspto-grants-1997_08
Patent number
US05653914

Reaction notes

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