Diethyl Ether → HCID 13282982, compound

HRID 647085Notes

Reaction equation

HRID 647085 reaction equation
C(OCC)C.C([Li])CCC.Br[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.[CH:18]([C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)=[O:19]>O1CCCC1>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([CH:18]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)[OH:19])[CH:13]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 61951-Naphthaldehyde2×HCID 122863-Bromopyridine2×HCID 178418339Butyllithium

Product 1

HCID 13282982HCID 13282982, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-120 °C

Procedure

To a 500 ml 3-neck flask round bottom flask equipped with an addition funnel, septum, thermometer and an argon inlet is added 100 ml of anhydrous diethyl ether and 62.5 ml of 1.6 molar butyllithium solution (in hexane). The system is cooled to -120° C. and 15.90 gm of 3-bromopyridine in 50 ml of tetrahydrofuran is added over 2 hours. After addition of the 3-bromopyridine, the system is stirred for an additional 45 minutes. At this time, 15.60 gm of 1-formylnaphthalene in 50 ml of tetrahydrofuran is added to the system while still maintaining a temperature of -120° C. The system is kept at -120° C. for an additional 3 hours after addition of the 1-formylnaphthalene and afterwards is allowed to come to room temperature. After 10 hours at room temperature, the system is quenched with saturated ammonium chloride (in water). The system is adjusted to pH 2 with HCl solution. The solution is extracted with diethyl ether. The aqueous solution is made basic with a 5% NaOH solution. The product is extracted with methylene chloride and dried over sodium sulfate. The methylene chloride is removed by stripping and the residue is triturated with hexane to give the 3-pyridyl-1-naphthylcarbinol.

Workup

  1. customTo a 500 ml 3-neck flask round bottom flask equipped with an addition funnel
  2. temperaturewhile still maintaining a temperature of -120° C
  3. waitThe system is kept at -120° C. for an additional 3 hours
  4. customto come to room temperature
  5. waitAfter 10 hours at room temperature
  6. customthe system is quenched with saturated ammonium chloride (in water)
  7. extractionThe solution is extracted with diethyl ether
  8. extractionThe product is extracted with methylene chloride
  9. dry with materialdried over sodium sulfate
  10. customThe methylene chloride is removed
  11. customthe residue is triturated with hexane

Sources & evidence

ORD record
ord-0d699c98542444ba828506254155cee9
Source dataset
uspto-grants-1983_10
Patent number
US04407806

Reaction notes

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