Hydrochloric Acid → HCID 178444338, compound

HRID 727760Notes

Reaction equation

HRID 727760 reaction equation
Br[C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1.C([Li])CCC.[CH2:18]([C@H:23]1[CH2:28][CH2:27][C@H:26]([C:29]2[CH:36]=[CH:35][C:32]([C:33]#N)=[CH:31][CH:30]=2)[CH2:25][CH2:24]1)[CH2:19][CH2:20][CH2:21][CH3:22].Cl.C1C[O:41]CC1>CCCCCC>[C:9]([C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:12])([F:11])[C:33]([C:32]2[CH:35]=[CH:36][C:29]([C@H:26]3[CH2:27][CH2:28][C@H:23]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:24][CH2:25]3)=[CH:30][CH:31]=2)=[O:41])=[CH:4][CH:5]=1)#[N:10]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 149935144-(Bromodifluoromethyl)benzonitrileHCID 178418339ButyllithiumHCID 178444331HCID 178444331, compound

Product 1

HCID 178444338HCID 178444338, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

0.08 mol of bromodifluoro(4-cyanophenyl)methane [prepared by the method of A. Haas, M. Spitzer, M. Lieb, Chem. Ber. 121 (1988)] are dissolved in 50 ml of THF; at -78°, 50 ml of a 1.6 molar solution of butyllithium in hexane are added dropwise. The mixture is stirred for 15 minutes, and then a solution of 0.08 mol of 4-(trans-4-pentylcyclohexyl)benzonitrile in 60 ml of THF is added dropwise. The mixture is allowed to warm to 0° and then poured into a mixture of ice and dilute hydrochloric acid. The organic phase is separated off, and the aqueous phase is extracted with ether (50 ml) and dichloromethane (2×25 ml). The organic phases are combined, the solvents are removed by distillation, and the residue is chromatographed on a silica gel column using petroleum ether/ether as the eluent. After the eluate has been evaporated, the residue is recrystallized from ethanol.

Workup

  1. temperatureto warm to 0°
  2. customThe organic phase is separated off
  3. extractionthe aqueous phase is extracted with ether (50 ml) and dichloromethane (2×25 ml)
  4. customthe solvents are removed by distillation
  5. customthe residue is chromatographed on a silica gel column
  6. customAfter the eluate has been evaporated
  7. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-54e9d826bc534a8f994bb4dff11c210b
Source dataset
uspto-grants-1991_09
Patent number
US05045229

Reaction notes

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