(1,1'-Biphenyl)-2-ol → HCID 59288369, compound

HRID 2420636Notes

Reaction equation

HRID 2420636 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].C1(C2C=CC=CC=2O)C=CC=CC=1.[F:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][C:30]=1I)[O:27][CH2:26][CH:25]([CH2:32][CH2:33][CH3:34])[CH2:24]2.[C:35]([O:43][CH2:44][CH3:45])(=[O:42])[CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38]>C1COCC1.[Cu]I.CCOCC>[F:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][C:30]=1[CH:36]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:35]([O:43][CH2:44][CH3:45])=[O:42])[O:27][CH2:26][CH:25]([CH2:32][CH2:33][CH3:34])[CH2:24]2

Participants

8

Reactant 4

HCID 7017(1,1'-Biphenyl)-2-olHCID 7761Diethyl MalonateHCID 10796Cesium carbonateHCID 592883606-Fluoro-7-iodo-3-propylchroman

Product 1

HCID 59288369HCID 59288369, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

17.0 g (52.2 mmol) of anhydrous caesium carbonate, 700 mg (3.67 mmol) of copper(I) iodide and 700 mg (4.11 mmol) of o-phenylphenol are initially introduced under dry nitrogen, a solution of 11.4 g (33.5 mmol) of 6-fluoro-7-iodo-3-propylchroman and 16.0 g (100 mmol) of diethyl malonate in 150 ml of THF is added, and the mixture is heated under reflux overnight. MTB ether is subsequently added to the batch, which is washed with dil. hydrochloric acid and dried over sodium sulfate. The solvent is removed in vacuo, and the crude product is purified by chromatography on silica gel with heptane/ethyl acetate (4:1). The product fraction (Rf=0.55) is reacted without further purification.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  3. washis washed with dil. hydrochloric acid
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed in vacuo
  6. customthe crude product is purified by chromatography on silica gel with heptane/ethyl acetate (4:1)
  7. customThe product fraction (Rf=0.55) is reacted without further purification

Sources & evidence

ORD record
ord-0832663d27f1466ab55f8cf3018134de
Source dataset
uspto-grants-2011_06
Patent number
US07955664B2

Reaction notes

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