Ammonium Chloride → HCID 12069389, compound

HRID 584293Notes

Reaction equation

HRID 584293 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:30]=1[CH2:31][OH:32])[CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:27])=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:23])[CH2:21][CH3:22])=[CH:16][C:15]=2[CH2:24][CH2:25][CH3:26])[CH:13]=1.[CH2:33]([Mg]Br)[CH3:34].[Cl-].[NH4+]>C1COCC1>[CH2:21]([C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:12]2[C:11]([CH3:27])=[CH:10][CH:9]=[C:8]([O:7][CH2:6][C:5]3[CH:28]=[CH:29][C:30]([CH2:31][OH:32])=[C:3]([CH2:2][OH:1])[CH:4]=3)[CH:13]=2)=[C:15]([CH2:24][CH2:25][CH3:26])[CH:16]=1)([OH:23])[CH2:33][CH3:34])[CH3:22]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 12069390HCID 12069390, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 12069389HCID 12069389, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

890 mg (2 mmol) of 1-{5′-[3,4-bis(hydroxymethyl)benzyloxy]-2′-methyl-2-propylbiphenyl-4-yl}-1-propanone are placed in 40 ml of dry THF in a round-bottomed flask and under a stream of nitrogen. At 0° C., 4.1 ml (12 mmol) of ethylmagnesium bromide are added. The reaction medium is stirred at room temperature for 1 hour 30 minutes and then poured into saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and then evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (50/50) to give 550 mg (64%) of {5-[4′-(1-ethyl-1-hydroxypropyl)-6-methyl-2′-propylbiphenyl-3-yloxymethyl]-2-hydroxymethylphenyl}methanol in the form of white crystals with a melting point of 97° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with a mixture of heptane and ethyl acetate (50/50)

Sources & evidence

ORD record
ord-6bc8176e491b457ca64a78d045300f0f
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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