Acetic Anhydride → 2-Acetoxy-5,5-dimethyl-3-(3-fluorophenyl)-4-(4-(methylsulfonyl)phenyl)-2,5-dihydrofuran

HRID 1106583Notes

Reaction equation

HRID 1106583 reaction equation
[CH3:1][C:2]1([CH3:25])[O:6][CH:5]([OH:7])[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[C:3]1[C:15]1[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=1.C(N(CC)CC)C.[C:33](OC(=O)C)(=[O:35])[CH3:34]>ClCCl.CN(C1C=CN=CC=1)C>[C:33]([O:7][CH:5]1[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[C:3]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[C:2]([CH3:25])([CH3:1])[O:6]1)(=[O:35])[CH3:34]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 98637875,5-Dimethyl-3-(3-fluorophenyl)-2-hydroxy-4-(4-methylsulfonylphenyl)-2,5-dihydrofuran

Product 1

HCID 187884902-Acetoxy-5,5-dimethyl-3-(3-fluorophenyl)-4-(4-(methylsulfonyl)phenyl)-2,5-dihydrofuran

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5,5-Dimethyl-3-(3-fluorophenyl)-2-hydroxy-4-(4-methylsulfonylphenyl)-2,5-dihydrofuran (Example 1, 0.8 g) and triethylamine (2 mL) in dichloromethane (20 mL) was added DMAP (5 mg) and acetic anhydride (1 mL). The resulting mixture was stirred at room temperature for 10 min, then quenched with CH2Cl2 and the aqueous NaHCO3. The mixture was extracted with CH2Cl2 and the organic phase was dried over Na2SO4, filtered and evaporated. The resulting solid was swished in 1:1 EtOAc/hexanes to provide 0.5 g of the title compound as a white solid.

Workup

  1. customquenched with CH2Cl2
  2. extractionThe mixture was extracted with CH2Cl2
  3. dry with materialthe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-9e3dfadee4b942a1be4a62d9a4236a20
Source dataset
uspto-grants-2000_05
Patent number
US06057319

Reaction notes

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