Hydrochloric Acid → alpha-[4-(Benzyloxy)-3-methoxyphenyl]-3-pyridinemethanol

HRID 2254703Notes

Reaction equation

HRID 2254703 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[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]=[O:30])[CH:24]=1.Cl>O1CCCC1>[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH:29]([C:25]2[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=2)[OH:30])=[CH:16][C:15]=1[O:21][CH3:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 103713-PyridinecarboxaldehydeHCID 36131281-(Benzyloxy)-4-bromo-2-methoxybenzeneHCID 178418306HCID 178418306, compound

Product 1

HCID 13365804alpha-[4-(Benzyloxy)-3-methoxyphenyl]-3-pyridinemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

aa) 10 ml of tert.butyl lithium solution (1.4M in hexane) are added dropwise at -70° within 10 minutes to 4.1 g of 4-(benzyloxy)-3-methoxy-bromobenzene dissolved in 40 ml of tetrahydrofuran. After stirring at -70° for 2 hours. 1 ml of pyridine-3-carbaldehyde is added within 5 minutes The reaction mixture is stirred at -70° for 1 hour and at 0° for 2 hours. and poured into 100 ml of 1N hydrochloric acid. The mixture is extracted three times with 50 ml of ether each time. The combined ether phases are washed with 100 ml of 1N hydrochloric acid and 20 nl of water. The combined aqueous phases are made alkaline with aqueous ammonia solution and extracted three times with 100 ml of methylene chloride each time. The combined methylene chloride phases are dried over sodium sulfate and evaporated. There is obtained alpha-[4-(benzyloxy)-3 -methoxyphenyl]-3-pyridinemethanol as an oil.

Workup

  1. stirringis stirred at -70° for 1 hour and at 0° for 2 hours
  2. extractionThe mixture is extracted three times with 50 ml of ether each time
  3. washThe combined ether phases are washed with 100 ml of 1N hydrochloric acid and 20 nl of water
  4. extractionextracted three times with 100 ml of methylene chloride each time
  5. dry with materialThe combined methylene chloride phases are dried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-ca7cc4d261194348a28a0165b901b3a9
Source dataset
uspto-grants-1993_08
Patent number
US05236952

Reaction notes

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