Tetrahydrofuran → HCID 67341991, compound

HRID 1669319Notes

Reaction equation

HRID 1669319 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:20])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([Br:19])[CH:12]=2)=[CH:6][CH:5]=1.C([Mg]Br)[CH:23]([CH3:25])[CH3:24].[CH2:28]1[CH2:32]OC[CH2:29]1>>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:5]=[CH:6][C:7]([C:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([Br:19])[CH:12]=2)([OH:20])[CH2:29][CH2:28][CH2:32][CH2:24][CH2:23][CH3:25])=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 67341888HCID 67341888, compoundHCID 178418816HCID 178418816, compound

Product 1

HCID 67341991HCID 67341991, compoundYield 10%

Procedure

To a solution of 4-(3-bromo-4-methoxy-benzoyl)-benzoic acid methyl ester (4.42 g, 12.66 mmol) in THF (20 mL) at 0° C. is added isobutylmagnesium bromide (2M, 7.6 mL). After stirring at room temperature for 2 hours, it is quenched with saturated ammonium chloride, extracted with EtOAc. The organic is concentrated to give 4-[1-(3-bromo-4-methoxy-phenyl)-1-hydroxy-heptyl]-benzoic acid methyl ester (0.572 g, 10%)

Workup

  1. customit is quenched with saturated ammonium chloride
  2. extractionextracted with EtOAc
  3. concentrationThe organic is concentrated

Sources & evidence

ORD record
ord-2dc58f668a7a4efcb58905b6b87ce724
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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