Water → HCID 58731009, compound

HRID 269545Notes

Reaction equation

HRID 269545 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:12]2[C:13]([C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=3[OH:25])=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36].O>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:12]2[C:13]([C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=3[O:25][CH2:33][CH2:34][CH:35]([CH3:37])[CH3:36])=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 78911-Bromo-3-methylbutaneHCID 11430Potassium CarbonateHCID 58730988HCID 58730988, compound

Product 1

HCID 58731009HCID 58731009, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-chloro-2-hydroxy-[1,1′;2′,1″]terphenyl-3″-carboxylic acid ethyl ester (50 mg, 0.14 mmol), potassium carbonate (48 mg, 0.35 mmol), and 1-bromo-3-methylbutane (23.5 mg, 0.15 mmol) was heated in N,N′-dimethylformamide (3 ml) at 90° C. for 4 hours. The reaction mixture was then poured into water and extracted with ethyl acetate; the organic layers were dried over MgSO4 and evaporated. The residue was chromatographed through a SPE column using 10% ethyl acetate in iso-hexane as eluent to yield the title compound as a white solid (45 mg, 75%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe organic layers were dried over MgSO4
  3. customevaporated
  4. customThe residue was chromatographed through a SPE column

Sources & evidence

ORD record
ord-999caeffcc924692b037169b76d680e2
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

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