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

HRID 2268224
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HRID 2268224 반응식
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
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참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-671d9bf3770f47f88525e4523b6afae7
출처 데이터셋
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06326510B1

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