Potassium Carbonate → HCID 23157441, compound

HRID 507935Notes

Reaction equation

HRID 507935 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:13][C:12]([C:22]([O:24][CH3:25])=[O:23])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]([O:28][CH2:29][CH2:30]Cl)[CH3:27].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:27][CH2:26][O:28][CH2:29][CH3:30])=[CH:17][CH:16]=2)=[CH:13][C:12]([C:22]([O:24][CH3:25])=[O:23])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium Carbonate2×HCID 12341Ethane, 1-chloro-2-ethoxy-2×HCID 23157554HCID 23157554, compound

Product 1

HCID 23157441HCID 23157441, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of methyl 6-(benzyloxy)-4′-hydroxybiphenyl-3-carboxylate (5.0 g, 15.0 mmol), 2-chloroethyl ethyl ether (2.1 mL, 19.1 mmol) and potassium carbonate (3.1 g, 22.4 mmol) in N,N-dimethylformamide (50 mL) was stirred at 60° C. for 24 hr. 2-Chloroethyl ethyl ether (2.0 mL, 18.2 mmol) and potassium carbonate (3.0 g, 21.8 mmol) were further added to the reaction solution, and the mixture was stirred at 60° C. for 2 days. The reaction solution was diluted with ethyl acetate, washed successively with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:10-1:3) to give the title compound (6.0 g, yield 99%) as a colorless oil.

Workup

  1. washwashed successively with water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1bf0da652a164fc2a58268d389dbc544
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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