HCID 22345611, compound → HCID 10195345, compound

HRID 584305Notes

Reaction equation

HRID 584305 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]([CH2:26][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][CH3:25])[CH:13]=1.[CH2:33]([Mg]Br)[CH3:34]>>[CH2:26]([C:11]1[C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH2:33][CH3:34])([OH:23])[CH2:21][CH3:22])=[CH:16][C:15]=2[CH2:24][CH3:25])=[CH:13][C:8]([O:7][CH2:6][C:5]2[CH:28]=[CH:29][C:30]([CH2:31][OH:32])=[C:3]([CH2:2][OH:1])[CH:4]=2)=[CH:9][CH:10]=1)[CH3:27]

Participants

3

Reactant 2

HCID 22345611HCID 22345611, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 10195345HCID 10195345, compound

Procedure

In a manner similar to that of Example 1(q), by reacting 840 mg (1.9 mmol) of 1-{5′-[3,4-bis(hydroxymethyl)benzyloxy]-2,2′-diethylbiphenyl-4-yl}-1-propanone with 5.2 ml (16 mmol) of ethylmagnesium bromide (3M/ether), and after purification by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (40/60), 254 mg (29%) of {5-[6,2′-diethyl-4′-(1-ethyl-1-hydroxypropyl)biphenyl-3-yloxymethyl]-2-hydroxymethylphenyl}methanol are obtained in the form of white crystals with a melting point of 93° C.

Workup

  1. customafter purification by chromatography on a column of silica
  2. washeluted with a mixture of heptane and ethyl acetate (40/60), 254 mg (29%) of {5-[6,2′-diethyl-4′-(1-ethyl-1-hydroxypropyl)biphenyl-3-yloxymethyl]-2-hydroxymethylphenyl}methanol
  3. customare obtained in the form of white crystals with a melting point of 93° C.

Sources & evidence

ORD record
ord-76251e013a8a461f959c72bd5d9809ce
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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