Hydrochloric Acid → HCID 19013830, compound

HRID 1728506Notes

Reaction equation

HRID 1728506 reaction equation
C([Li])CCC.[CH2:6]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=3[F:30])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)[CH2:7][CH2:8][CH2:9][CH3:10].[CH:31](=[O:34])[CH2:32][CH3:33].Cl>CCCCCC.O1CCCC1>[CH2:6]([C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([CH:31]([OH:34])[CH2:32][CH3:33])=[C:25]([F:29])[C:24]=3[F:30])=[CH:19][CH:18]=2)=[CH:15][CH:16]=1)[CH2:7][CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 527PropanalHCID 19013787HCID 19013787, compoundHCID 178418339Butyllithium

Product 1

HCID 19013830HCID 19013830, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

6.45 ml of 1.6N butyllithium solution in n-hexane are added dropwise within 5 minutes at -50° C. to a solution of 3.15 g of 1-[4-(4-pentylphenyl)-phenyl]-2,3-difluorobenzene and the reaction mixture is left to react at the same temperature for 3 hours. Then, a solution of 652 mg of propionaldehyde in 4 ml of tetrahydrofuran is added and the mixture is left to warm slowly to room temperature. After 15 hours it is treated with 10 ml of 1N hydrochloric acid, partitioned between methylene chloride and water, the organic phase is washed with saturated sodium bicarbonate solution and dried over anhydrous magnesium sulphate. Evaporation of the solvent and chromatography of the residue on silica gel with 5-20% ethyl acetate in petroleum ether gives 3.2 g of 1-[4-(4-pentylphenyl)-phenyl]-2,3-difluoro-4(1-hydroxypropyl)-benzene.

Workup

  1. waitthe reaction mixture is left
  2. customto react at the same temperature for 3 hours
  3. waitthe mixture is left
  4. custompartitioned between methylene chloride and water
  5. washthe organic phase is washed with saturated sodium bicarbonate solution
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customEvaporation of the solvent and chromatography of the residue on silica gel with 5-20% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-c807ab9c208a42258871b109a5e6c206
Source dataset
uspto-grants-1994_07
Patent number
US05328637

Reaction notes

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