Pentanal → HCID 14499204, compound

HRID 1194505Notes

Reaction equation

HRID 1194505 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.C[Li].C([Li])(C)(C)C.[CH:20](=[O:25])[CH2:21][CH2:22][CH2:23][CH3:24]>CCOCC>[OH:25][CH:20]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2)[CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 8063PentanalHCID 271446-Bromo-2-naphthalenolHCID 178418306HCID 178418306, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 14499204HCID 14499204, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 1.00 g (4.48 mmol, Aldrich) of 6-bromo-2-naphthol in 40 ml of dry ether at -78° was added dropwise 3.2 ml (1.4M in ether, 5.0 mmol) of methyllithium solution. The reaction mixture was stirred for 5 minutes then 5.0 ml (1.8M in pentane, 9.0 mmol) of t-butyllithium solution was added over 5 minutes. The resulting slurry was stirred at -78° C. for 30 minutes then at 0° for 15 minutes, re-cooled to -78° and a solution of 0.50 ml (4.7 mmol) of distilled valeraldehyde in 3 ml of ether was added dropwise over several minutes. After 5 minutes the reaction mixture was warmed to 0°, quenched with 1 ml of H2O, added to 100 ml of ice-cold saturated aqueous NH4Cl solution. The organic layer was separated, washed with 100 ml of H2O, dried (MgSO4) and concentrated in vacuo to give a dark oil. The crude oil was purified by flash chromatography (10×5.0 cm, 1:3 EtOAc/petroleum ether) to afford 590 mg (57%) of title compound as a pale yellow solid, m.p. 109°-111°.

Workup

  1. stirringThe resulting slurry was stirred at -78° C. for 30 minutes
  2. waitat 0° for 15 minutes
  3. temperaturere-cooled to -78°
  4. temperatureAfter 5 minutes the reaction mixture was warmed to 0°
  5. customquenched with 1 ml of H2O
  6. additionadded to 100 ml of ice-cold saturated aqueous NH4Cl solution
  7. customThe organic layer was separated
  8. washwashed with 100 ml of H2O
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo
  11. customto give a dark oil
  12. customThe crude oil was purified by flash chromatography (10×5.0 cm, 1:3 EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-581c9c8b16754756ada574cd15d10c2f
Source dataset
uspto-grants-1989_03
Patent number
US04814454

Reaction notes

Loading…