2,2'-Bipyridine → HCID 178445812, compound

HRID 1016724Notes

Reaction equation

HRID 1016724 reaction equation
[OH-].[K+].N1C=CC=CC=1C1C=CC=CN=1.[C:15]([CH:19]1[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]1)([CH3:18])([CH3:17])[CH3:16]>CC(O)C>[C:15]([C@@H:19]1[CH2:20][CH2:21][C@H:22]([OH:25])[CH2:23][CH2:24]1)([CH3:18])([CH3:16])[CH3:17].[C:15]([C@H:19]1[CH2:20][CH2:21][C@H:22]([OH:25])[CH2:23][CH2:24]1)([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 3

HCID 14742,2'-BipyridineHCID 73924-tert-ButylcyclohexanoneHCID 14797Potassium Hydroxide

Product 2

HCID 178445811HCID 178445811, compoundYield 8.6%HCID 178445812HCID 178445812, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

RuClCp* (cod) (3.8 mg, 0.01 mmol), KOH (0.04 mmol), 2,2′-bipyridyl (3.1 mg, 0.02 mmol) and 4-t-butylcyclohexanone (385.63 mg, 2.5 mmol) were dissolved into 10 ml of 2-propanol, and deaerated by argon substitution, after which the total amount of the resulting mixture was transferred into a 100-milliliter metallic autoclave. Then, the reaction was started at room temperature (28° C.) while conducting argon substitution. After the reaction solution was stirred for 18 hours, the reaction produces, cis-4-t-butylcyclohexanol (yield 8.6%) and trans-4-t-butylcyclohexanol (yield 21.1%), were identified and quantitatively determined by TLC monitor (silica gel: n-hexane/ethyl acetate=4/1) and gas chromatography of the reaction solution. Here, 35.0% of the raw material, 4-t-butylcyclohexanone, was recovered.

Workup

  1. customwas started at room temperature
  2. custom(28° C.)
  3. customthe reaction produces

Sources & evidence

ORD record
ord-99519967588c43488394062fde61dfd4
Source dataset
uspto-grants-2002_11
Patent number
US06476278B1

Reaction notes

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