Potassium Carbonate → HCID 9911928, compound

HRID 1841284Notes

Reaction equation

HRID 1841284 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([O:14][CH2:15][CH3:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].Br[CH2:19][CH:20]=[C:21]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH2:25][CH2:24][C:23]2[CH:32]=[CH:33][CH:34]=[CH:35][C:22]1=2.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C1C=CC=CC=1>[CH:32]1[C:23]2[CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:21](=[CH:20][CH2:19][O:13][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][CH:5]([O:14][CH2:15][CH3:16])[C:4]([O:3][CH2:1][CH3:2])=[O:17])=[CH:12][CH:11]=3)[C:22]=2[CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1201707HCID 1201707, compoundHCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 9911928HCID 9911928, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl2-ethoxy-3-(4-hydroxyphenyl)-propionate (2.38 g, 0.01 mol), 5-(2-bromo-1-ethylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (2.75 g, 0.01 mol) and potassium carbonate (5.14 g, 0.03 mol) in dimethylformamide (30 ml) was heated at 100° C. for 20 h. The reaction mixture was diluted with benzene (80 ml), washed with 5% aqueous citric acid (3×25 ml) and with saturated NaHCO3 (25 ml), dried (MgSO4) and evaporated. The residue (4.88 g) was purified by column chromatography on silica gel (benzene eluent) to yield the title compound; 2.3 g (53.7%).

Workup

  1. washwashed with 5% aqueous citric acid (3×25 ml) and with saturated NaHCO3 (25 ml)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue (4.88 g) was purified by column chromatography on silica gel (benzene eluent)

Sources & evidence

ORD record
ord-608ac7a962f54637a715a600b826f202
Source dataset
uspto-grants-2004_01
Patent number
US06683111B2

Reaction notes

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