1-Pentanol → 2-Methyl-acrylic acid 6-[4-(2-pentoxycarbonyl-vinyl)-phenoxy]-hexyl ester

HRID 1810716Notes

Reaction equation

HRID 1810716 reaction equation
[OH:1][C:2]([CH:4]=[CH:5][C:6]1[CH:24]=[CH:23][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18](=[O:22])[C:19]([CH3:21])=[CH2:20])=[CH:8][CH:7]=1)=[O:3].[CH2:25](O)[CH2:26][CH2:27][CH2:28][CH3:29].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1>[CH2:25]([O:3][C:2]([CH:4]=[CH:5][C:6]1[CH:24]=[CH:23][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18](=[O:22])[C:19]([CH3:21])=[CH2:20])=[CH:8][CH:7]=1)=[O:1])[CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 62761-PentanolHCID 10868DicyclohexylcarbodiimideHCID 67322679HCID 67322679, compound

Product 1

HCID 673230262-Methyl-acrylic acid 6-[4-(2-pentoxycarbonyl-vinyl)-phenoxy]-hexyl ester

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a 250-mL round-bottom flask were added 2-methyl-acrylic acid 6-[4-(2-hydroxycarbonyl-vinyl)-phenoxy]-hexyl ester (4.98 g, 15.0 mmol), 1-pentanol (1.785 mL, 16.5 mmol) and 4-dimethylaminopyridine (DMAP,92 mg, 0.75 mmol) as solids and a stirbar. The flask was purged with N2, followed by the addition of CH2Cl2 (35 mL). The suspension was stirred at room temperature for 20 min to give a white slurry. The flask was cooled in an ice bath and N,N′-dicyclohexylcarbodiimide (DCC, 3.25 g, 15.75 mmol) was introduced. The mixture quickly became a light yellow solution, which was then removed from the ice bath and stirred at room temperature. After 20 h, the resulting white slurry was loaded on a SiO2 column (˜100 g) for quick purification. The product was eluted off with 10% EtOAc in hexanes. The fractions with the desired product were combined, concentrated and then dried in vacuo to a clear oil, which turned into a white solid (Addition Monomer 6) upon cooling (5.45 g, 90%).

Workup

  1. customThe flask was purged with N2
  2. additionfollowed by the addition of CH2Cl2 (35 mL)
  3. customto give a white slurry
  4. temperatureThe flask was cooled in an ice bath
  5. customwas then removed from the ice bath
  6. stirringstirred at room temperature
  7. waitAfter 20 h
  8. customthe resulting white slurry was loaded on a SiO2 column (˜100 g) for quick purification
  9. washThe product was eluted off with 10% EtOAc in hexanes
  10. concentrationconcentrated
  11. customdried in vacuo to a clear oil, which
  12. temperatureupon cooling (5.45 g, 90%)

Sources & evidence

ORD record
ord-d33cd7c9af4541e19561d9931d3146e1
Source dataset
uspto-grants-2013_01
Patent number
US08362151B2

Reaction notes

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