Diethyl Ether → HCID 70523198, compound

HRID 1649480Notes

Reaction equation

HRID 1649480 reaction equation
C(OCC)C.C([Li])CCC.Br[C:12]1[CH:13]=[N:14][CH:15]=[N: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:13]=[CH:12][CH:17]=[N:16][C:15]=1[C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:24]=1[CH:23]=[CH:22][CH:21]=[C:20]2[CH2:18][OH:19]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 61951-Naphthaldehyde2×HCID 783445-Bromopyrimidine2×HCID 178418339Butyllithium

Product 1

HCID 70523198HCID 70523198, 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 5-bromopyrimidine in 50 ml of tetrahydrofuran is added over 2 hours. After addition of the 5-bromopyrimidine, 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 pH2 with HCl solution. The product is extracted with methylene chloride. The methylene chloride is washed with a 10% NaOH solution and then is dried over sodium sulfate. The methylene chloride is removed by stripping and the residue is triturated with hexane to give the 5-pyrimidyl-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 product is extracted with methylene chloride
  8. washThe methylene chloride is washed with a 10% NaOH solution
  9. dry with materialis dried over sodium sulfate
  10. customThe methylene chloride is removed
  11. customthe residue is triturated with hexane

Sources & evidence

ORD record
ord-79fd3e0ba7b54c9590e8f3ea905c024e
Source dataset
uspto-grants-1983_11
Patent number
US04417050

Reaction notes

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