HCID 22345643, compound → HCID 10174128, compound

HRID 584307Notes

Reaction equation

HRID 584307 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[CH2:24][CH2:25][CH3:26])[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[CH2:24][CH2:25][CH3:26])=[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 22345643HCID 22345643, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 10174128HCID 10174128, compound

Procedure

In a manner similar to that of Example 1(q), by reacting 830 mg (1.9 mmol) of 1-{5′-[3,4-bis(hydroxymethyl)benzyloxy]-2′-ethyl-2-propylbiphenyl-4-yl}-1-propanone with 5.1 ml (15.2 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), 700 mg (77%) of {4-[6-ethyl-4′-(1-ethyl-1-hydroxypropyl)-2′-propylbiphenyl-3-yloxymethyl]-2-hydroxymethylphenyl}methanol are obtained in the form of white crystals with a melting point of 101° C.

Workup

  1. customafter purification by chromatography on a column of silica
  2. washeluted with a mixture of heptane and ethyl acetate (40/60), 700 mg (77%) of {4-[6-ethyl-4′-(1-ethyl-1-hydroxypropyl)-2′-propylbiphenyl-3-yloxymethyl]-2-hydroxymethylphenyl}methanol
  3. customare obtained in the form of white crystals with a melting point of 101° C.

Sources & evidence

ORD record
ord-bff009dd9d2f410994a5cc5454f7d741
Source dataset
uspto-grants-2005_08
Patent number
US06924400B2

Reaction notes

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