1-Naphthaldehyde → 1-(1-Naphthyl)-1-propanol

HRID 2293677

Reaction equation

HRID 2293677 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[C:5]1([CH:15]=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1>O1CCCC1>[C:5]1([CH:15]([OH:16])[CH2:1][CH3:2])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 61951-NaphthaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 124533351-(1-Naphthyl)-1-propanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a flame-dried flask containing 8.0 mL of dry tetrahydrofuran under an argon atmosphere cooled to -78° C. Is added 4.0 mL (3.0 M) of a solution of ethylmagnesium bromide in tetrahydrofuran. The stirrable mixture is treated with a solution of 1.36 g of commercially available 1-naphthaldehyde in 4.0 mL of tetrahydrofuran with a 2 mL rinse. The reaction is stirred at -78° C. for 5 minutes then warmed to room temperature. After 1 hour the mixture is re-cooled to 0° C., carefully quenched with saturated ammonium chloride, and diluted with diethyl ether. The layers are separated; organic phase washed with brine, dried (magnesium sulfate), and concentrated under reduced pressure. The residue is flash column chromatographed using 25% ethyl acetate in hexane to give 1.76 g of the title product as a pale pink oil.

Workup

  1. washrinse
  2. temperaturethen warmed to room temperature
  3. temperatureAfter 1 hour the mixture is re-cooled to 0° C.
  4. customcarefully quenched with saturated ammonium chloride
  5. additiondiluted with diethyl ether
  6. customThe layers are separated
  7. washorganic phase washed with brine
  8. dry with materialdried (magnesium sulfate)
  9. concentrationconcentrated under reduced pressure
  10. customchromatographed

Sources & evidence

ORD record
ord-a3bae3ce05c84673a4f3379e3f30c941
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Linked notes

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