Hexane → HCID 19006051, compound

HRID 1742823Notes

Reaction equation

HRID 1742823 reaction equation
C([Li])CCC.CCCCCC.Br[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.[CH3:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C:22]1=[O:27]>C(OCC)C.O>[CH3:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C:22]1([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)[OH:27]

Participants

7

Reactant 4

HCID 8058HexaneHCID 142684-BromopyridineHCID 1109982-MethoxycyclohexanoneHCID 178418339Butyllithium

Product 1

HCID 19006051HCID 19006051, compoundYield 38.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

A stirred solution of 2.5M n-butyllithium in hexane (30.8ml, 0.77mol) at -78° C. was mixed with diethyl ether (310ml) and a solution of 4-bromopyridine (60.9g, 0.39mol) in diethyl ether (1200 ml) was added dropwise over 3 hours. Stirring was continued for 2 hours and a solution of 2-methoxycyclohexanone (54.3g, 0.42mol) in diethyl ether (total volume 100ml) was added dropwise over 1 hour. The stirred solution was allowed to warm to room temperature and stirring was continued overnight. Water (250ml) was then added to the reaction mixture, keeping the temperature below 20° C. and the mixture stirred for a further 30 minutes. The organic layer was separated and the aqueous layer was extracted with diethyl ether (3×50ml). The combined organic layers were extracted with hydrochloric acid (2N, 2×250ml+100ml) and the combined acidic extracts brought to pH 11 with 5N aqueous sodium hydroxide and extracted with ethyl acetate (3×250ml). The combined ethyl acetate extracts were dried (MgSO4) and evaporated in vacuo. The residue was recrystallized from petroleum ether (60°-80° C.) to give (±)-2-methoxy-l-(pyrid-4-yl)cyclohexanol (32.0g, 0.15mol) as a mixture of cis and trans isomers, m.p. 98°-101° C.

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. customthe temperature below 20° C.
  4. stirringthe mixture stirred for a further 30 minutes
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with diethyl ether (3×50ml)
  7. extractionThe combined organic layers were extracted with hydrochloric acid (2N, 2×250ml+100ml)
  8. extractionextracted with ethyl acetate (3×250ml)
  9. dry with materialThe combined ethyl acetate extracts were dried (MgSO4)
  10. customevaporated in vacuo
  11. customThe residue was recrystallized from petroleum ether (60°-80° C.)

Sources & evidence

ORD record
ord-2922f12155a24cd1b77ccd4f9fc93d8b
Source dataset
uspto-grants-1994_08
Patent number
US05342848

Reaction notes

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