tert-Butyl acrylate → HCID 66716176, compound

HRID 2173765Notes

Reaction equation

HRID 2173765 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][OH:15])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Na].[C:17]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:20])[CH:18]=[CH2:19]>C1COCC1>[N:1]1([CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:19][CH2:18][C:17]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 15458tert-Butyl acrylateHCID 36123337037-28-7HCID 5360545Sodium

Product 1

HCID 66716176HCID 66716176, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 989 mg of 2-[2-(2-morpholin-4-yl-ethoxy)-ethoxy]-ethanol in 2.8 mL of anhydrous THF was added 1.04 mg of sodium. After heating at 40° C. for 2 hours 15 minutes, 793 μL of tert-butyl acrylate were added. After heating for a further two hours at 40° C., the reaction mixture was left for 20 hours at room temperature and then concentrated under reduced pressure and purified by flash chromatography on silica (Merck SuperVarioPrep 70 g column, Si60 15-40 μm), using a gradient of 0 to 6% MeOH in DCM. The fractions containing the desired product were combined and concentrated under reduced pressure. 1 g of tert-butyl 3-{2-[2-(2-morpholin-4-yl-ethoxy)-ethoxy]-ethoxy}-propanoate were obtained. LC/MS (E): tr (ELSD)=0.59 min; [M+H]+: m/z 348

Workup

  1. temperatureAfter heating for a further two hours at 40° C.
  2. concentrationconcentrated under reduced pressure
  3. custompurified by flash chromatography on silica (Merck SuperVarioPrep 70 g column, Si60 15-40 μm)
  4. additionThe fractions containing the desired product
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-061d5761ed454e07b96f372d68c314a1
Source dataset
uspto-grants-2015_06
Patent number
US09056914B2

Reaction notes

Loading…