Water → alpha-[4-(Benzyloxy)-3-methoxyphenyl]-4-quinolinemethanol

HRID 2260323Notes

Reaction equation

HRID 2260323 reaction equation
C([Li])(C)(C)C.[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17](Br)=[CH:16][C:15]=1[O:21][CH3:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]([CH:33]=[O:34])=[CH:25][CH:24]=1.O>O1CCCC1.C(O)(=O)C>[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH:33]([C:26]2[C:27]3[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:23]=[CH:24][CH:25]=2)[OH:34])=[CH:16][C:15]=1[O:21][CH3:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 780724-QuinolinecarboxaldehydeHCID 36131281-(Benzyloxy)-4-bromo-2-methoxybenzeneHCID 178418306HCID 178418306, compound

Product 1

HCID 21459134alpha-[4-(Benzyloxy)-3-methoxyphenyl]-4-quinolinemethanol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

25 ml of tert.-butyllithium solution (1.4M in hexane) are added dropwise at -70° within 10 minutes to 10 g of 4-(benzyloxy)-3-methoxy-bromobenzene dissolved in 100 ml of tetrahydrofuran. After stirring at -70° for 1 hour, 5 g of quinoline-4-carbaldehyde dissolved in 50 ml of tetrahydrofuran are added dropwise within 30 minutes. The reaction mixture is stirred at -40° for 1 hour and at -5° for 1 hour, poured into 200 ml of water and adjusted to pH 4 with glacial acetic acid. The mixture is extracted three times with 50 ml of ether each time. The combined ether phases are washed with water, dried over sodium sulfate and evaporated. There is obtained α-[4-(benzyloxy)-3-methoxyphenyl]-4-quinolinemethanol as an amorphous solid.

Workup

  1. additionare added dropwise within 30 minutes
  2. stirringThe reaction mixture is stirred at -40° for 1 hour and at -5° for 1 hour
  3. extractionThe mixture is extracted three times with 50 ml of ether each time
  4. washThe combined ether phases are washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-ad1202283b1149f78034235930d547eb
Source dataset
uspto-grants-1995_12
Patent number
US05476875

Reaction notes

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