Tetrahydrofuran → p-Benzyl-ethylaminophenethyl acrylate

HRID 1174439Notes

Reaction equation

HRID 1174439 reaction equation
[CH2:1]([C:8]1[CH:19]=[CH:18][C:11]([CH2:12][CH:13]([OH:17])[NH:14][CH2:15][CH3:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[O:27]1C[CH2:30][CH2:29][CH2:28]1.C([O-])(=O)C=C.[Cl-]>C1(C)C=CC=CC=1.O>[C:28]([O:17][CH:13]([NH:14][CH2:15][CH3:16])[CH2:12][C:11]1[CH:18]=[CH:19][C:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:9][CH:10]=1)(=[O:27])[CH:29]=[CH2:30]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 21924244Chloride acrylateHCID 68771578p-Benzyl-ethylaminophenethyl alcohol

Product 1

HCID 68771319p-Benzyl-ethylaminophenethyl acrylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

In a three-aperture flask, 6.64 g (26 mmol) of p-benzyl-ethylaminophenethyl alcohol, 5.79 g (57.2 mmol) of triethylamine, and 50 mL of dehydrated tetrahydrofuran were poured, and the mixture was stirred under an argon atmosphere and an ice-cooling condition. Then, 4.70 g (52 mmol) of chloride acrylate was delivered by drops into the reaction solution for 30 minutes. Upon completion of the dripping, the reaction solution was further stirred for 3 hours. The reaction solution was poured to 100 mL of water and then an extract was obtained therefrom by using toluene, followed by washing with water three times. The toluene solution was dried with anhydrous magnesium sulfate, and then the solvent was distilled away to purify the toluene solution by silica gel chromatography using a mixture solvent of hexane/ethyl acetate (5/1) as an eluent to thereby synthesize 3.21 g (yield: 40% by mass) of p-benzyl-ethylaminophenethyl acrylate of the exemplified compound No. 22 represented by the following structural formula.

Workup

  1. stirringUpon completion of the dripping, the reaction solution was further stirred for 3 hours
  2. customan extract was obtained
  3. washby washing with water three times
  4. dry with materialThe toluene solution was dried with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away
  6. customto purify the toluene solution by silica gel chromatography
  7. customto thereby synthesize 3.21 g (yield: 40% by mass) of p-benzyl-ethylaminophenethyl acrylate of the exemplified compound No

Sources & evidence

ORD record
ord-1c94f8146a6741abbe04370430a8594a
Source dataset
uspto-grants-2010_11
Patent number
US07838188B2

Reaction notes

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