Potassium Carbonate → HCID 9805094, compound

HRID 1841287Notes

Reaction equation

HRID 1841287 reaction equation
[CH:1]1[C:11]2[CH:10]([CH2:12][CH2:13][OH:14])[S:9][C:8]3[CH:15]=[CH:16][CH:17]=[CH:18][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.CS(Cl)(=O)=O.O[C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH:32]([O:38][CH2:39][CH3:40])[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1.CN(C)C=O.O.C(N(CC)CC)C>[CH2:39]([O:38][CH:32]([CH2:31][C:28]1[CH:27]=[CH:26][C:25]([O:14][CH2:13][CH2:12][CH:10]2[S:9][C:8]3[CH:15]=[CH:16][CH:17]=[CH:18][C:7]=3[O:6][C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:11]2=3)=[CH:30][CH:29]=1)[C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH3:40]

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 23445966HCID 23445966, compound

Product 1

HCID 9805094HCID 9805094, compound

Reagents, catalysts & solvents 4

HCID 241BenzeneSolvent2×HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-(11H-5-oxa-10-thia-dibenzo[a,d]cyclohepten-11-yl)-ethanol (4.1 g, 15.9 mmol) and triethylamine (5 ml) in benzene (80 ml) was treated with methanesulfonyl chloride (2.8 g, 24 mmol) and the mixture stirred for 2 h. The resulting reaction mixture was treated with water (50 ml) and the phases were separated. The organic phase was dried (MgSO4) and the solvent evaporated, affording a residue, which was dissolved in dimethylformamide (10 ml). To this solution were added ethyl 3-(4-hydroxyphenyl)2-ethoxypropionate (3.8 g, 16 mmol) and potassium carbonate (2.8 g, 20 mmol), and the mixture was heated to 100° C. for 10 h. Water (100 ml) and benzene (150 ml) were added, and the organic phase was collected and washed with water (2×50 ml), dried (K2CO3) and evaporated. The resulting residue was purified by column chromatography on silica gel (benzene and chloroform as eluents) to give the title compound as an oil: 4.6 g (60%).

Workup

  1. customThe resulting reaction mixture
  2. customthe phases were separated
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customthe solvent evaporated
  5. customaffording a residue, which
  6. customthe organic phase was collected
  7. washwashed with water (2×50 ml)
  8. dry with materialdried (K2CO3)
  9. customevaporated
  10. customThe resulting residue was purified by column chromatography on silica gel (benzene and chloroform as eluents)

Sources & evidence

ORD record
ord-33d2812145594218b15d6fddf3b29baa
Source dataset
uspto-grants-2004_01
Patent number
US06683111B2

Reaction notes

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