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2-Methylbenzoic acid → 6-(2-Methoxy-4-methoxymethoxyphenyl)-5-(4-methylbenzoyloxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 1043676
ノート
印刷プレビュー

反応式

HRID 1043676 の反応式
[OH:1][CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH3:22])=[CH:15][C:14]=2[O:23][CH3:24])=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([CH3:27])=[CH:6][C:7]([CH3:26])([CH3:25])[NH:8]2.C[C:29]1[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=1[C:31]([OH:33])=O.[CH2:38](P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1C=CC=CC=1.CCCCCC>[CH3:24][O:23][C:14]1[CH:15]=[C:16]([O:19][CH2:20][O:21][CH3:22])[CH:17]=[CH:18][C:13]=1[C:12]1[C:3]([CH2:2][O:1][C:31](=[O:33])[C:30]2[CH:29]=[CH:37][C:36]([CH3:38])=[CH:35][CH:34]=2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:26])([CH3:25])[CH:6]=[C:5]2[CH3:27]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 83732-Methylbenzoic acidHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 579905855-Hydroxymethyl-6-(2-methoxy-4-methoxymethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

生成物 1

HCID 579905836-(2-Methoxy-4-methoxymethoxyphenyl)-5-(4-methylbenzoyloxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline収率 73.2%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 8058Hexane溶媒

実験手順

5-Hydroxymethyl-6-(2-methoxy-4-methoxymethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 1, 1.00 g, 2.71 mmol), 2-methylbenzoic acid (739 mg, 5.43 mmol), tri-n-butylphosphine (1.35 mL, 5.40 mmol), and 1,1′-(azodicarbonyl)dipiperidine (1.37 g, 5.43 mmol) were dissolved in anhydrous benzene (30 mL), and then the mixture was stirred under argon atmosphere at room temperature overnight. Hexane (30 mL) was added to the reaction mixture, and then the unsoluble materials were filtered out. The filtrate was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (967 mg) as a colorless amorphous product. (Yield 73%)

後処理

  1. filtrationthe unsoluble materials were filtered out
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-c7da24d070c544b286c32d9c127d467c
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08563551B2

反応ノート

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