4'-Chloro[1,1'-biphenyl]-4-carbaldehyde → HCID 22760362, compound

HRID 1391748Notes

Reaction equation

HRID 1391748 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)=O.CC(C)=O.[CH2:23]([Mg]Cl)[CH2:24][CH2:25][CH3:26]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([OH:15])[CH2:23][CH2:24][CH2:25][CH3:26])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 5925704'-Chloro[1,1'-biphenyl]-4-carbaldehydeHCID 18522661Acetone cardiceHCID 178418265HCID 178418265, compound

Product 1

HCID 22760362HCID 22760362, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 4′-chloro-4-biphenylcarbaldehyde (200 mg, 0.92 mmol) in anhydrous THF (10 mL) under nitrogen at −78° C. (dry ice/acetone) was added nBuMgCl (550 μL of a 2M solution in THF, 1.10 mmol). The reaction mixture was stirred at −78° C. for 1 hour and then at rt for 18 hours. The reaction was quenched by cautious addition of water (15 mL) and extracted with EtOAc (3×20 mL). The combined organic extract was then dried (MgSO4) and reduced under vacuum. Purification by flash chromatography (silica), eluting with cyclohexane:EtOAc (9:1) afforded the title compound as a colourless gum (140 mg).

Workup

  1. waitat rt for 18 hours
  2. customThe reaction was quenched by cautious addition of water (15 mL)
  3. extractionextracted with EtOAc (3×20 mL)
  4. extractionThe combined organic extract
  5. dry with materialwas then dried (MgSO4)
  6. customPurification by flash chromatography (silica)
  7. washeluting with cyclohexane:EtOAc (9:1)

Sources & evidence

ORD record
ord-34b5fb2d9a1c4343a43f51104d6ea7e0
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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