Potassium bisulfate → HCID 10526643, compound

HRID 37724Notes

Reaction equation

HRID 37724 reaction equation
[CH3:1][Mg]Br.[F:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]([C:21]2[C:26]([O:27][CH3:28])=[C:25]([CH3:29])[C:24]([CH3:30])=[C:23]([CH:31]=[O:32])[C:22]=2[CH3:33])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:7][CH:6]=1.S([O-])(O)(=O)=O.[K+]>O1CCCC1>[F:4][C:5]1[CH:6]=[CH:7][C:8]([C@H:11]([C:21]2[C:26]([O:27][CH3:28])=[C:25]([CH3:29])[C:24]([CH3:30])=[C:23]([CH:31]([OH:32])[CH3:1])[C:22]=2[CH3:33])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 10787945methyl (R)-7-(4-fluorophenyl)-7-(3-formyl-6-methoxy-2,4,5-trimethylphenyl)heptanoateHCID 178418573HCID 178418573, compound

Product 1

HCID 10526643HCID 10526643, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of methylmagnesium bromide in tetrahydrofuran (1M, 54.3 ml) was added anhydrous tetrahydrofuran (90 ml). To the solution was added dropwise a solution of methyl (R)-7-(4-fluorophenyl)-7-(3-formyl-6-methoxy-2,4,5-trimethylphenyl)heptanoate (4.5 g, 10.9 mmol) in tetrahydrofuran (20 ml) at -78° C., followed by stirring for 30 minutes at the same temperature. To the reaction mixture, an aqueous solution of potassium hydrogensulfate, followed by subjected to extraction with ethyl acetate. The organic layer was washed with water, an aqueous solution of sodium hydrogencarbonate and water, in the order mentioned, and dried over magnesiumsulfate. The organic layer was distilled off under reduced pressure, and the residue was subjected to a silica gel column chromatography to give methyl (R)-7-(4-fluorophenyl)-7-[3-(1-hydroxyethyl)-6-methoxy-2,4,5-trimethylphenyl]heptanoate (4.4 g). Physico-chemical properties and spectral data of this compound are shown in [Table 5].

Workup

  1. extractionby subjected to extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesiumsulfate
  4. distillationThe organic layer was distilled off under reduced pressure

Sources & evidence

ORD record
ord-57bb0195911344f893d37090067e63de
Source dataset
uspto-grants-1995_05
Patent number
US05420363

Reaction notes

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