Diethyl Ether → HCID 19967113, compound

HRID 326249

Reaction equation

HRID 326249 reaction equation
[Mg].O(CC)CC.Br[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[N:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH:24]=[O:25])[CH:22]=2)[CH:17]=[CH:16][CH:15]=1>O1CCCC1>[C:8]1([CH:24]([C:21]2[CH:22]=[C:23]3[C:18]([CH:17]=[CH:16][CH:15]=[N:14]3)=[CH:19][CH:20]=2)[OH:25])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7961BromobenzeneHCID 47122557-QuinolinecarboxaldehydeHCID 5462224Magnesium

Product 1

HCID 19967113HCID 19967113, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 1.25 parts of magnesium, 14 parts of 1,1'-oxybisethane and 8 parts of bromobenzene was added a solution of 8 parts of intermediate 1, namely 7-quinolinecarboxaldehyde, in 72 parts of tetrahydrofuran, keeping the temperature between 0° C. and 5° C. After stirring for 12 hours at room temperature, the reaction mixture was poured into 300 parts of ice-water. The product was extracted with 1,1'-oxybisethane (3×70 parts). The combined extracts were dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 98:2). The eluent of the desired fraction was evaporated, yielding 3.2 parts (26.6%) of α-phenyl-7-quinolinemethanol; mp. 118° C. (interm. 2). In a similar manner there were also prepared the intermediates listed in Table 1.

Workup

  1. customthe temperature between 0° C. and 5° C
  2. extractionThe product was extracted with 1,1'-oxybisethane (3×70 parts)
  3. customThe combined extracts were dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 98:2)
  7. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-ea6fb0e3e27a49cb991618f183d458d6
Source dataset
uspto-grants-1993_12
Patent number
US05268380

Linked notes

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