Potassium bisulfate → HCID 15125160, compound

HRID 373388Notes

Reaction equation

HRID 373388 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:18]2[C:23]([O:24][CH3:25])=[C:22]([CH3:26])[C:21]([CH3:27])=[C:20]([CH:28]=[O:29])[C:19]=2[CH3:30])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH:3]=1.S([O-])(O)(=O)=O.[K+]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:18]2[C:23]([O:24][CH3:25])=[C:22]([CH3:26])[C:21]([CH3:27])=[C:20]([CH:28]([OH:29])[CH2:7][CH2:2][CH2:3][CH3:4])[C:19]=2[CH3:30])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 516920Potassium bisulfateHCID 15125156HCID 15125156, compound

Product 1

HCID 15125160HCID 15125160, compoundYield 132.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution methyl 7-(4-fluorophenyl)-7-(3-formyl-6-methoxy-2,4,5-trimethylphenyl)heptanoate (3.7 g) in anhydrous tetrahydrofuran (75 ml) was added 1.6 M solution of n-butyl lithium-hexane (6.2 ml) at -78° C. over 25 minutes. The mixture was stirred at the same temperature for 1 hour and aqueous potassium hydrogen sulfate was added. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was subjected to silica gel column chromatography to obtain methyl 7-(4-fluorophenyl)-7-[3-(1-hydroxypentyl)-6-methoxy-2,4,5-trimethylphenyl)heptanoate (2.8 g) (Compound 65). The physical properties and spectrum data thereof are shown in Tables 3 and 4.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated saline
  3. dry with materialdried with anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-54ffab9445284eaa88258931b15f9a3b
Source dataset
uspto-grants-1992_11
Patent number
US05162571

Reaction notes

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