Water → HCID 70213312, compound

HRID 2268217Notes

Reaction equation

HRID 2268217 reaction equation
[CH2:1]1[CH2:5][O:4][CH2:3][CH2:2]1.C([N:8]([CH2:11][CH3:12])CC)C.[CH3:13][C:14]1([CH3:29])[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[C:20]2[CH:19]=[C:18]([C:26](Cl)=[O:27])[CH:17]=[CH:16][C:15]1=2.[OH2:30]>>[CH3:13][C:14]1([CH3:29])[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[C:20]2[CH:19]=[C:18]([C:26]([NH:8][C:11]3[CH:12]=[CH:3][CH:2]=[CH:1][C:5]=3[CH:2]=[CH:1][C:5]([O:4][CH3:3])=[O:30])=[O:27])[CH:17]=[CH:16][C:15]1=2

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 27954665,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl chloride

Product 1

HCID 70213312HCID 70213312, compound

Procedure

1.13 g (6.38 mmol) of methyl 2-aminophenyl acrylate, 30 ml of THF and 1 ml (7 mmol) of triethylamine are introduced into a round-bottomed flask. A solution of 1.6 g (6.38 mmol) of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthoyl chloride is added dropwise and the mixture is stirred at room temperature for three hours. The reaction medium is poured into water and extracted with ethyl acetate, and the organic phase is separated out after settling has taken place, washed with water, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (95/5). After evaporating the solvents, 2.3 g (92%) of methyl 3-{2-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenecarbonyl)amino]phenyl}acrylate, with a melting point of 95-6° C., are collected.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase is separated out after settling
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a mixture of heptane and ethyl acetate (95/5)
  9. customAfter evaporating the solvents, 2.3 g (92%) of methyl 3-{2-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthalenecarbonyl)amino]phenyl}acrylate
  10. customwith a melting point of 95-6° C., are collected

Sources & evidence

ORD record
ord-d439329f8bef43e39cf9564244ebcb11
Source dataset
uspto-grants-2001_12
Patent number
US06326510B1

Reaction notes

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