Triethylamine → HCID 58741029, compound

HRID 899493Notes

Reaction equation

HRID 899493 reaction equation
[CH3:1][CH:2]1[O:10][C:5]2([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[O:6][CH:7]([CH3:9])[CH2:8][N:4]2[CH2:3]1.C(N(CC)CC)C.[C:24](Cl)(=[O:28])[C:25]([CH3:27])=[CH2:26]>C(Cl)(Cl)Cl>[CH3:1][CH:2]1[O:10][C:5]2([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:24](=[O:28])[C:25]([CH3:27])=[CH2:26])[O:6][CH:7]([CH3:9])[CH2:8][N:4]2[CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 68824103HCID 68824103, compound

Product 1

HCID 58741029HCID 58741029, compoundYield 462%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

In an oven dried 100 mL round-bottom flask equipped with a pressure equalizing addition funnel and a reflux condenser were added 5-(2,6-Dimethyl-tetrahydro-oxazolo[2,3-b]oxazol-7a-yl)-pentan-1-ol (22.9 g, 0.01 mol) followed by chloroform 50 mL and triethylamine 12.12 g, 0.12 mol). The reaction content was cooled to 0° C. under nitrogen. While stirring a solution of methacryloyl chloride (11.44 g, 0.11 mol) in chloroform was added slowly. After completion of the acid chloride the reaction was stirred one hour at 0° C., then allowed to warmed to room temperature and then stirred over night at room temperature. The triethylamine salt was filter off through Celite® (World Minerals, Santa Barbara, Calif.), the filtrate concentrate at reduced pressure. NMR (proton) showed this material to be the desired material contaminated with triethyl amine salt. This material was then washed with hexanes (2×125 ml), the hexanes washes combined concentrated giving 13.74 g of product.

Workup

  1. customIn an oven dried 100 mL round-bottom flask
  2. customequipped with a pressure
  3. additionaddition funnel and a reflux condenser
  4. additionwas added slowly
  5. temperatureto warmed to room temperature
  6. filtrationThe triethylamine salt was filter off through Celite® (World Minerals, Santa Barbara, Calif.)
  7. concentrationthe filtrate concentrate at reduced pressure
  8. washThis material was then washed with hexanes (2×125 ml)
  9. concentrationcombined concentrated

Sources & evidence

ORD record
ord-3fa4aba04e464432aeb76f4b8aa9600d
Source dataset
uspto-grants-2008_04
Patent number
US07355050B2

Reaction notes

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