Hexane → HCID 131718352, compound

HRID 22132Notes

Reaction equation

HRID 22132 reaction equation
C([Li])CCC.CCCCCC.[C:12]([O:16][C:17]([NH:19][CH:20]1[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([Br:30])[CH:26]=2)[CH2:21]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]=[O:38])[CH:32]=1>O1CCCC1>[C:12]([O:16][C:17]([NH:19][CH:20]1[CH2:29][CH2:28][C:27]2[CH2:26][C:25]([CH:37]([C:33]3[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=3)[OH:38])([Br:30])[CH:24]=[CH:23][C:22]=2[CH2:21]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 8058HexaneHCID 103713-PyridinecarboxaldehydeHCID 10064926133277-10-8HCID 178418339Butyllithium

Product 1

HCID 131718352HCID 131718352, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

8.8 ml of a solution of n-butyl lithium in hexane (2.5 mol) was dropped to a solution of 3.25 g of 2-tert.butoxycarbonylamino-6-bromo-1,2,3,4-tetrahydro-naphthaline in 50 ml of absolute tetrahydrofurane cooled to -70° C. and stirring was continued for 1.5 hours at -50° C. Subsequently, 1.1 g of pyridine-3-aldehyde were dropped into the mixture at -70° C. After stirring for one hour, the reaction mixture was poured on ice and extracted with ethyl acetate. The organic phase was washed with water, dried and evaporated. The obtained residue was recrystallised from cyclohexane/ethyl acetate.

Workup

  1. stirringAfter stirring for one hour
  2. additionthe reaction mixture was poured on ice
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated
  7. customThe obtained residue was recrystallised from cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-3aaf35dd5e8f4bbd94ef8b44feecaefe
Source dataset
uspto-grants-1995_06
Patent number
US05426119

Reaction notes

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