HCID 178418361, compound → HCID 178444260, compound

HRID 1906333Notes

Reaction equation

HRID 1906333 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH:24]=[CH:25][C@H:26]4[CH2:31][CH2:30][C@H:29]([C:32]5[CH:37]=[CH:36][C:35]([C:38]6[CH:43]=[CH:42][C:41]([C:44]#[N:45])=[CH:40][CH:39]=6)=[CH:34][CH:33]=5)[CH2:28][CH2:27]4)=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[H][H]>O1CCCC1.[Pd]>[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C@H:26]4[CH2:27][CH2:28][C@H:29]([C:32]5[CH:33]=[CH:34][C:35]([C:38]6[CH:39]=[CH:40][C:41]([C:44]#[N:45])=[CH:42][CH:43]=6)=[CH:36][CH:37]=5)[CH2:30][CH2:31]4)=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178444259HCID 178444259, compound

Product 1

HCID 178444260HCID 178444260, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.214 g of 4'-[trans-4-[2-(4'-(trans-4-pentylcyclohexyl)-4-biphenylyl)vinyl]cyclohexyl]-4-biphenylcarbonitrile in 200 ml of tetrahydrofuran was treated with 52.5 mg of palladium/carbon (5%) and hydrogenated at room temperature until the hydrogen uptake came to a stand-still (1.75 hours). The reaction mixture was subsequently gassed with nitrogen and suction filtered (rinsing with hot tetrahydrofuran). After concentrating the filtrate in vacuo and drying at 50° C. under a water-jet vacuum there was obtained 0.310 g of colourless, solid 4'-[trans-4-[2-(4'-(trans-4-pentylcyclohexyl)-4-biphenylyl)ethyl]cyclohexyl]-4-biphenylcarbonitrile which still contained solvent. Recrystallization from tetrahydrofuran gave colourless needles with (S-N) 194.5° C. and cl.p. (N-I) 440° C.

Workup

  1. customcame to a stand-still (1.75 hours)
  2. filtrationfiltered
  3. wash(rinsing with hot tetrahydrofuran)
  4. concentrationAfter concentrating the filtrate in vacuo
  5. customdrying at 50° C. under a water-jet vacuum

Sources & evidence

ORD record
ord-38c65bbcaff94b1e9315b7ced2928bc0
Source dataset
uspto-grants-1987_03
Patent number
US04652089

Reaction notes

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