Methyl Acrylate → HCID 19834309, compound

HRID 2051070Notes

Reaction equation

HRID 2051070 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].[OH:7][N:8]1[C:13]([CH3:15])([CH3:14])[CH2:12][CH:11]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][O:25][CH:26]3[CH2:31][C:30]([CH3:33])([CH3:32])[N:29]([OH:34])[C:28]([CH3:36])([CH3:35])[CH2:27]3)=[CH:20][CH:19]=2)[CH2:10][C:9]1([CH3:38])[CH3:37].CC(C)([O-:42])C.[K+].[O:45]1[CH2:49][CH2:48][CH2:47][CH2:46]1>CCOCC>[CH3:6][O:5][C:1]([CH2:2][CH2:3][O:34][N:29]1[C:28]([CH3:36])([CH3:35])[CH2:27][CH:26]([O:25][CH2:24][C:21]2[CH:22]=[CH:23][C:18]([CH2:17][O:16][CH:11]3[CH2:12][C:13]([CH3:14])([CH3:15])[N:8]([O:7][CH2:48][CH2:47][C:46]([O:45][CH3:49])=[O:42])[C:9]([CH3:38])([CH3:37])[CH2:10]3)=[CH:19][CH:20]=2)[CH2:31][C:30]1([CH3:33])[CH3:32])=[O:4]

Participants

6

Reactant 4

HCID 7294Methyl AcrylateHCID 8028TetrahydrofuranHCID 19768329HCID 19768329, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19834309HCID 19834309, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

Methyl acrylate (64.9 grams, 750 mmol) is rapidly added under a nitrogen atmosphere to a mixture of 16.9 grams (38 mmol) of alpha,alpha'-bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yloxy)-p-xylene, 0.85 gram of potassium tert-butoxide and 70 ml of tetrahydrofuran. The reaction is exothermic and the temperature exceeds 40° C. for one hour. The reaction mixture is then heated at 60° C. for four hours and allowed to stand overnight at ambient temperature. The reaction mixture is diluted with ether (300 ml), washed consecutively with saturated sodium bicarbonate solution (200 ml), water (4×500 ml), and saturated sodium chloride solution (200 ml), dried over anhydrous magnesium sulfate and evaporated to an oil. The oil is stirred with methanol and a precipitate forms. The supernatant liquid is concentrated to give a solid which is purified by flash chromatography (silica gel; 9:1 hexane:ethyl acetate) to afford 4.6 grams (20% yield) of the title compound as a white solid melting at 84°-85° C.

Workup

  1. waitto stand overnight at ambient temperature
  2. washwashed consecutively with saturated sodium bicarbonate solution (200 ml), water (4×500 ml), and saturated sodium chloride solution (200 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated to an oil
  5. concentrationThe supernatant liquid is concentrated
  6. customto give a solid which
  7. customis purified by flash chromatography (silica gel; 9:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-a40e3393c0934e4baa5d650a7a0615b8
Source dataset
uspto-grants-1991_05
Patent number
US05015678

Reaction notes

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