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

HRID 273199

반응식

HRID 273199 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide촉매

반응 조건

온도
115 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d5ce02cecbb44429899fff1cda686101
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456214B2

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