Diethyl Ether → HCID 13236916, compound

HRID 647084Notes

Reaction equation

HRID 647084 reaction equation
C(OCC)C.C([Li])CCC.Br[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.[Cl:18][C:19]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:20]=1[CH:21]=[O:22]>O1CCCC1>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([CH:21]([C:20]2[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:19]=2[Cl:18])[OH:22])[CH:13]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 122863-Bromopyridine2×HCID 134042,4-Dichlorobenzaldehyde2×HCID 178418339Butyllithium

Product 1

HCID 13236916HCID 13236916, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-120 °C

Procedure

To a 500 ml 3-neck round bottom flask equipped with an addition funnel, septum, thermometer and an argon inlet was added 150 ml of anhydrous diethyl ether and 94 ml of 1.6 molar butyllithium solution (in hexane). The system was cooled to -120° C. and 14.5 ml of 3-bromopyridine in 75 ml of tetrahydrofuran was added over 1 hour. After addition of the 3-bromopyridine, the system was stirred for an additional 45 minutes. At this time, 26.25 gm of 2,4-dichlorobenzaldehyde in 75 ml of tetrahydrofuran was added to the system while still maintaining at temperatures of -120° C. The system was kept at -120° C. for an additional 6 hours after addition of the 2,4-dichlorobenzaldehyde and afterwards allowed to come to room temperature. After 10 hours at room temperature, the system was quenched with saturated ammonium chloride (in water). The system was then adjusted to a pH 2 with concentrated HCl solution. The solution was extracted with diethyl ether. The aqueous solution was made basic with a 50% NaOH solution. The product was extracted with methylene chloride and then dried over sodium sulfate. The methylene chloride was removed by stripping to give 25.75 gm of the 3-pyridyl-2,4-dichlorophenyl-carbinol as tan solid, m.p. 108°-111° C., and listed as compound number 2 in Table I.

Workup

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

Sources & evidence

ORD record
ord-91a5055f7d0542b09cc7349291e3b7fc
Source dataset
uspto-grants-1983_10
Patent number
US04407806

Reaction notes

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