Triethylamine → HCID 67323709, compound

HRID 896726Notes

Reaction equation

HRID 896726 reaction equation
[CH2:1]([O:17][C:18](=[O:35])[CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][OH:34])=[CH:23][CH:22]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(N(CC)CC)C.[C:43](Cl)(=[O:47])[C:44]([CH3:46])=[CH2:45].[OH-].[K+]>O1CCCC1>[CH2:1]([O:17][C:18]([CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][O:34][C:43](=[O:47])[C:44]([CH3:46])=[CH2:45])=[CH:23][CH:22]=1)=[O:35])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 14797Potassium HydroxideHCID 69764959HCID 69764959, compound

Product 1

HCID 67323709HCID 67323709, compoundYield 12.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled solution of 3-[4-(6-hydroxy-hexyloxy)-phenyl]-acrylic acid hexadecyl ester (2.6 g, 5.3 mmol), triethylamine (0.99 ml, 7.4 mmol) and 4 crystals of BHT in tetrahydrofuran (30 ml) was added dropwise methacryloyl chloride (0.68 g, 6.9 mmol). The reaction mixture was allowed to react for 7.5 hours, warming to room temperature. Potassium hydroxide solution (5 wt %, 50 ml) was added and the solution extracted 3×100 ml ethyl acetate. The combined organic layers were washed with 100 ml portions of 1M HCl, water, brine and then dried with magnesium sulfate and concentrated. The crude product was purified by silica gel chromatography eluting with 10% ethyl acetate in hexane, followed by recrystallization from hexane, to give 0.37 g white solid, 95% pure by HPLC. H1 NMR (CDCl3): 7.65 (d, 1H, J=16 Hz), 7.49 (d, 2H, J=8.7 Hz), 6.90 (d, 2H, J=8.8 Hz), 6.33 (d, 1H, J=15.8 Hz), 6.12 (m, 1H), 5.57 (m, 1H), 4.19 (m, 4H), 4.00 (m, 2H), 1.96 (m, 3H), 1.8-1.4 (m, 8H), 1.28 (s, 32H), 0.90 (vt, 3H).

Workup

  1. customto react for 7.5 hours
  2. extractionthe solution extracted 3×100 ml ethyl acetate
  3. washThe combined organic layers were washed with 100 ml portions of 1M HCl, water, brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with 10% ethyl acetate in hexane
  8. customfollowed by recrystallization from hexane

Sources & evidence

ORD record
ord-957a3731669f4af288f545e05eb16e9d
Source dataset
uspto-grants-2005_07
Patent number
US06919404B2

Reaction notes

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