Acetone → HCID 18655679, compound

HRID 37723Notes

Reaction equation

HRID 37723 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:17]2[C:22]([OH:23])=[C:21]([CH3:24])[C:20]([CH3:25])=[C:19]([CH:26]=[O:27])[C:18]=2[CH3:28])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1.[BH4-].[Na+].CC(C)=O>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([C:17]2[C:18]([CH3:28])=[C:19]([CH2:26][OH:27])[C:20]([CH3:25])=[C:21]([CH3:24])[C:22]=2[OH:23])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 10524208(R)-7-(4-fluorophenyl)-7-(3-formyl-6-hydroxy-2,4,5-trimethylphenyl)heptanoic acid

Product 1

HCID 18655679HCID 18655679, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-7-(4-fluorophenyl)-7-(3-formyl-6-hydroxy-2,4,5-trimethylphenyl)heptanoic acid (0.43 g, 1.1 mmol) in tetrahydrofuran (7 ml) was added, under ice-cooling, sodium borohydride (21.0 mg). The mixture was stirred for two hours at room temperature, to which was added acetone, then the solvent was distilled off under reduced pressure. The residue was neutralized with 1N HCl, which was subjected to extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous saline solution, followed by drying over magnesium sulfate. The solvent was distilled off under reduced pressure to leave 0.38 g of (R)-7-(4-fluorophenyl)-7-(2-hydroxy-5-hydroxymethyl-3,4,6-trimethylphenyl)heptanoic acid, whose spectral data are shown in [Table 4].

Workup

  1. temperaturecooling
  2. distillationthe solvent was distilled off under reduced pressure
  3. extractionwas subjected to extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialby drying over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cddc9d9add9e41a28f3ab7665366740f
Source dataset
uspto-grants-1995_05
Patent number
US05420363

Reaction notes

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