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

HRID 273199
Notes
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Reaction equation

HRID 273199 reaction equation
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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 9964923
3-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide
Catalyst

Conditions

Temperature
115 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d5ce02cecbb44429899fff1cda686101
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07456214B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes