Hydrochloric Acid → HCID 13365804, compound

HRID 274432Notes

Reaction equation

HRID 274432 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 13365804HCID 13365804, compound

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 ml 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. stirringThe reaction mixture is 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 ml 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-d5228a64ac4745ecb47e1a28a26920ee
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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