3-Phenoxybenzaldehyde → HCID 16735089, compound

HRID 899571Notes

Reaction equation

HRID 899571 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]1([Li])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[O:1]([C:8]1[CH:9]=[C:10]([CH:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[OH:12])[CH:13]=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 382843-PhenoxybenzaldehydeHCID 178506676HCID 178506676, compound

Product 1

HCID 16735089HCID 16735089, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 3-phenoxybenzaldehyde (2 g, 10.09 mmol) in THF (15 mL) at −78° C. was added phenyllithium (6.73 mL, 1.8M solution in cyclohexane-ether) dropwise. After stirring under argon at −78° C. for 4 hrs, the reaction was quenched with water and extracted with diethyl ether. The organic layer was washed with brine, dried with magnesium sulfate, filtered, and concentrated under reduced pressure to give the crude product. The crude mixture was purified via flash SiO2 chromatography (ethyl acetate/hexanes (10%/90%) to (20%/80%)) to give 128 (2.79 g, 86% yield): 1H-NMR (400 MHz, chloroform-d) δ 6.87-7.38 (m, 10H), 7.09 (m, 1H), 6.99 (app d, J=7.3 Hz, 1H), 6.88 (m, J=8.6, 2.2 Hz, 1H), 5.81 (s, 4H).

Workup

  1. customthe reaction was quenched with water
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product
  8. customThe crude mixture was purified via flash SiO2 chromatography (ethyl acetate/hexanes (10%/90%) to (20%/80%))

Sources & evidence

ORD record
ord-53217933de584f818423054191ac2417
Source dataset
uspto-grants-2008_04
Patent number
US07355079B2

Reaction notes

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