Diethyl Ether → HCID 19967126, compound

HRID 1756512Notes

Reaction equation

HRID 1756512 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.O(CC)CC.C([Li])CCC.[N:16]1[C:25]2[C:20](=[CH:21][C:22]([CH:26]=[O:27])=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1>O1CCCC1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:26]([C:22]1[CH:21]=[C:20]2[C:25](=[CH:24][CH:23]=1)[N:16]=[CH:17][CH:18]=[CH:19]2)[OH:27]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8030ThiopheneHCID 7656536-QuinolinecarbaldehydeHCID 178418339Butyllithium

Product 1

HCID 19967126HCID 19967126, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred and cooled (-5°/0° C.) solution of 5.4 parts of thiophene in 21.3 parts of 1,1'-oxybisethane were added portionwise 43.5 parts of a solution of n. butyllithium in hexanes 1.6M. After stirring for 20 min. at 0° C., there was added a solution of 5 parts of intermediate 16, namely 6-quinolinecarboxaldehyde, in 71.2 parts of tetrahydrofuran. Stirring at 0° C. was continued for 1 hour and then the reaction mixture was poured into 200 parts of ice-water. The product was extracted with 1, 1'-oxybisethane and the extract was dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2C12 /CH3OH 95:5). The eluent of the desired fraction was evaporated, yielding 2.4 parts (31.1%) of α-(2-thienyl)-6-quinolinemethanol (interm. 17).

Workup

  1. additionwere added portionwise 43.5 parts of a solution of n
  2. stirringAfter stirring for 20 min. at 0° C.
  3. stirringStirring at 0° C.
  4. extractionThe product was extracted with 1, 1'-oxybisethane
  5. customthe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography (silica gel
  9. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-168887d1e2a3494a8106d955387bf58d
Source dataset
uspto-grants-1995_08
Patent number
US05441954

Reaction notes

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