Cerium(III) chloride → HCID 18385745, compound

HRID 2298313Notes

Reaction equation

HRID 2298313 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11](=[O:27])[C:12]([CH3:26])([CH3:25])[O:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+].[Cl-].[Ce+3].[Cl-].[Cl-]>O>[CH3:26][C:12]1([CH3:25])[C:11](=[O:27])[C:10]([C:7]2[CH:8]=[CH:9][C:4]([CH:1]([OH:3])[CH3:2])=[CH:5][CH:6]=2)=[C:14]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[O:13]1

Participants

5

Reactant 3

HCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 11222843HCID 11222843, compound

Product 1

HCID 18385745HCID 18385745, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(4-acetylphenyl)-2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone (150 mg, Example 10), sodium borohydride(35mg) and cerium(III) chloride (20 mg) in 40 ml methaol was stirred at room temperature for 12 hours, which was followed by addition of water. Then the methanol was removed in vacuo and the resulting aqueous solution was extracted with ethylacetate. The ethylacetate layer was concentrated under reduced pressure and was purified by column chromatography (hexane/ethylacetate=1:1) to obtain 100 mg of 2,2-dimethyl-4-{4-(1-hydroxyethyl)phenyl}-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone. NMR: δ1.51-1.53 (d, J=6.3 Hz, 3H), 1.58 (s, 6H), 3.07 (s, 3H), 4.90-4.97 (q, J=6.3 Hz, 1H), 7.25-7.28 (m, 2H), 7.39-7.42 (m, 2H), 7.84-7.86 (m, 2H), 7.92-7.95 (m, 2H). IR (cm−1): 3502, 2977, 1696, 1594, 1317, 1149 960, 771.

Workup

  1. customThen the methanol was removed in vacuo
  2. extractionthe resulting aqueous solution was extracted with ethylacetate
  3. concentrationThe ethylacetate layer was concentrated under reduced pressure
  4. customwas purified by column chromatography (hexane/ethylacetate=1:1)

Sources & evidence

ORD record
ord-622d8bf7443c425f80eaa7245d0e7f9e
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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