Water → (E)-N-Methoxy-N-methyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)acrylamide

HRID 2268224Notes

Reaction equation

HRID 2268224 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].C(N(CC)CC)C.[CH3:13][C:14]1([CH3:31])[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[C:20]2[CH:19]=[C:18]([CH:26]=[CH:27][C:28](Cl)=[O:29])[CH:17]=[CH:16][C:15]1=2.O>C1COCC1>[CH3:5][O:4][N:3]([CH3:2])[C:28](=[O:29])/[CH:27]=[CH:26]/[C:18]1[CH:17]=[CH:16][C:15]2[C:14]([CH3:31])([CH3:13])[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[C:20]=2[CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 734315563-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyl chloride

Product 1

HCID 18349873(E)-N-Methoxy-N-methyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)acrylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

727 mg (7.45 mmol) of N,O-dimethylhydroxyl-amine hydrochloride, 10 ml of THF and 2.3 ml (16.4 mmol) of triethylamine are introduced into a three-necked flask under a stream of nitrogen. A solution of 2.06 g (7.45 mmol) of 3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)acryloyl chloride prepared in Example 1(c) in 20 ml of THF is added dropwise and the mixture is stirred at room temperature for six 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, 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 (80/20). After evaporating the solvents, 1 g (45%) of (E)-N-methoxy-N-methyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)acrylamide is collected in the form of an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase is separated out after settling
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with a mixture of heptane and ethyl acetate (80/20)
  8. customAfter evaporating the solvents, 1 g (45%) of (E)-N-methoxy-N-methyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)acrylamide
  9. customis collected in the form of an oil

Sources & evidence

ORD record
ord-671d9bf3770f47f88525e4523b6afae7
Source dataset
uspto-grants-2001_12
Patent number
US06326510B1

Reaction notes

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