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Triethylamine → 3-(3',4',5'-Trimethoxybenzoyl)-7-methoxy-8-hydroxy-2h-chromene

HRID 273199
ノート
印刷プレビュー

反応式

HRID 273199 の反応式
CN(C)[CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=1)=[O:6].[OH:20][C:21]1[C:28]([OH:29])=[C:27]([O:30][CH3:31])[CH:26]=[CH:25][C:22]=1C=O.[CH3:32]CN(CC)CC>[Br-].C([N+]1C(C)=C(CCO)SC=1)C>[CH3:18][O:17][C:9]1[CH:8]=[C:7]([CH:12]=[C:11]([O:13][CH3:14])[C:10]=1[O:15][CH3:16])[C:5]([C:4]1[CH2:31][O:30][C:27]2[C:26]([CH:3]=1)=[CH:25][CH:22]=[C:21]([O:20][CH3:32])[C:28]=2[OH:29])=[O:6]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 4123063-(Dimethylamino)-1-(3,4,5-trimethoxyphenyl)propan-1-oneHCID 115573522,3-Dihydroxy-4-methoxybenzaldehyde

生成物 1

HCID 115162603-(3',4',5'-Trimethoxybenzoyl)-7-methoxy-8-hydroxy-2h-chromene収率 11%

試薬・触媒・溶媒 1

HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide
触媒

反応条件

温度
115 °C

実験手順

A mixture of 2-(N,N-dimethylamino)ethyl-(3′,4′,5′-trimethoxyphenyl)ketone (4, 1.17 g, 4.37 mmol), 2,3-dihydroxy-4-methoxybenzaldehyde (2, 0.74 g, 4.37 mmol), 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (0.12 g, 0.44 mmol) and Et3N (1 ml) was heated under reflux at 115° C. for 3.5 hours. After quenching with 1M HCl, the product was extracted with CH2Cl2. The combined extract was washed with water, rinsed with brine and dried over anhydrous magnesium sulfate. Purification was done by silica gel flash column chromatography (60:40, hexane-ethyl acetate) which afforded the pure yellow-colored phenol (0.179 g, 0.48 mmol) in 11% yield. The phenol had a melting point of 189-190° C.

後処理

  1. temperaturewas heated
  2. customAfter quenching with 1M HCl
  3. extractionthe product was extracted with CH2Cl2
  4. extractionThe combined extract
  5. washwas washed with water
  6. washrinsed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customPurification

出典と根拠

ORDレコード
ord-d5ce02cecbb44429899fff1cda686101
出典データセット
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07456214B2

反応ノート

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