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Methyl Acrylate → HCID 19784863, compound

HRID 2051069
Notes
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Reaction equation

HRID 2051069 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][C:13]([CH3:16])([CH3:15])[N:12]([OH:17])[C:11]([CH3:19])([CH3:18])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S([O-])([O-])(=O)=O.[Mg+2].CC(C)([O-])C.[K+].[C:32]([O:36][CH3:37])(=[O:35])[CH:33]=[CH2:34]>[Pd].O1CCCC1>[CH2:1]([O:8][CH:9]1[CH2:14][C:13]([CH3:15])([CH3:16])[N:12]([O:17][CH2:34][CH2:33][C:32]([O:36][CH3:37])=[O:35])[C:11]([CH3:19])([CH3:18])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 7294Methyl AcrylateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 9838139HCID 9838139, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19784863HCID 19784863, compoundYield 48.9%

Reagents, catalysts & solvents 2

HCID 23938
Palladium
Catalyst
HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
55 °C

Procedure

A mixture of 20.0 grams (76 mmol) of 4-benzyloxyl-oxyl-2,2,6,6-tetramethylpiperidine, 10.0 grams of anhydrous magnesium sulfate, 500 mg of 5% palladium on carbon and 150 ml of tetrahydrofuran is hydrogenated on a Parr apparatus (50 psi, ambient temperature). Catalyst and drying agent are removed by filtration and the filtrate is quickly transferred to a flask under a nitrogen atmosphere. To the flask are added 0.85 gram of potassium tert-butoxide, 19.7 grams (229 mmol) of methyl acrylate, and 50 ml of tetrahydrofuran. The reaction mixture is stirred at ambient temperature for three hours and at 55° C. for one hour. The reaction mixture is partitioned between ether (300 ml) and saturated sodium bicarbonate solution (150 ml). The ether layer is washed with water (2×500 ml), washed with saturated aqueous sodium chloride (200 ml), dried over anhydrous magnesium sulfate and concentrated to an oil. The oil is purified by flash chromatography (silica gel; 9:1 hexane:ethyl acetate) to afford 13.0 grams of the title compound as a colorless liquid.

Workup

  1. customis hydrogenated on a Parr apparatus (50 psi, ambient temperature)
  2. customCatalyst and drying agent
  3. customare removed by filtration
  4. customthe filtrate is quickly transferred to a flask under a nitrogen atmosphere
  5. customThe reaction mixture is partitioned between ether (300 ml) and saturated sodium bicarbonate solution (150 ml)
  6. washThe ether layer is washed with water (2×500 ml)
  7. washwashed with saturated aqueous sodium chloride (200 ml)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated to an oil
  10. customThe oil is purified by flash chromatography (silica gel; 9:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-87803e8794af44caa0b9099434a386fd
Source dataset
uspto-grants-1991_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05015678

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes