HCID 22345631, compound → HCID 15948786, compound

HRID 584310Notes

Reaction equation

HRID 584310 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][C:31]=1[CH2:32][OH:33])[CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:27][CH3:28])=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:23])[CH2:21][CH3:22])=[CH:16][C:15]=2[CH:24]([CH3:26])[CH3:25])[CH:13]=1.[CH2:34]([Mg]Br)[CH3:35]>>[CH2:27]([C:11]1[C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH2:34][CH3:35])([OH:23])[CH2:21][CH3:22])=[CH:16][C:15]=2[CH:24]([CH3:26])[CH3:25])=[CH:13][C:8]([O:7][CH2:6][C:5]2[CH:29]=[CH:30][C:31]([CH2:32][OH:33])=[C:3]([CH2:2][OH:1])[CH:4]=2)=[CH:9][CH:10]=1)[CH3:28]

Participants

3

Reactant 2

HCID 22345631HCID 22345631, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 15948786HCID 15948786, compound

Procedure

In a manner similar to that of Example 1(q), by reacting 810 mg (1.8 mmol) of 1-{5′-[3,4-bis(hydroxymethyl)benzyloxy]-2′-ethyl-2-isopropylbiphenyl-4-yl}-1-propanone with 4.8 ml (15 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 (35/65), 600 mg (70%) of {4-[6-Ethyl-4′-(1-ethyl-1-hydroxypropyl)-2′-isopropylbiphenyl-3-yloxymethyl]-2-hydroxymethylphenyl}methanol are obtained in the form of white crystals with a melting point of 109° C.

Workup

  1. customafter purification by chromatography on a column of silica
  2. washeluted with a mixture of heptane and ethyl acetate (35/65), 600 mg (70%) of {4-[6-Ethyl-4′-(1-ethyl-1-hydroxypropyl)-2′-isopropylbiphenyl-3-yloxymethyl]-2-hydroxymethylphenyl}methanol
  3. customare obtained in the form of white crystals with a melting point of 109° C.

Sources & evidence

ORD record
ord-804f3a8d7fe34564a02e8ffbcb0a451f
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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