Sodium hydride → HCID 59463768, compound

HRID 1713339Notes

Reaction equation

HRID 1713339 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3](=[O:17])[CH2:4][C:5]1([CH3:16])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[O:8][CH2:7][CH2:6]1.[CH3:20][S+](C)(C)=O.[H-].[Na+].[I-].C[S+](C)(C)=O>CS(C)=O>[F:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2([CH3:16])[CH2:4][C:3]1([C:2]([F:1])([F:18])[F:19])[CH2:20][O:17]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 74499TrimethylsulfoxoniumHCID 57809915HCID 57809915, compound

Product 1

HCID 59463768HCID 59463768, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of 950 mg (3.45 mmol) of 1,1,1-trifluoro-3-(6-fluoro-4-methylchroman-4-yl)propan-2-one in 10 mL of anhydrous DMSO was added 3.5 mL (4.2 mmol) of a 1.2 M solution of trimethylsulfoxonium ylide, which was prepared by reacting 1.45 g (36.3 mmol) of sodium hydride (60% in mineral oil) with 8 g (36.3 mmol) of trimethylsulfoxonium iodide in 30 mL of DMSO. After 2 hours, the mixture was poured onto ice-cold saturated aqueous ammonium chloride and extracted with 150 mL of ether in several portions. The combined organic layers were washed with four portions of water, then washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 930 mg (93%) of 6-fluoro-4-methyl-4(2-trifloromethyloxiranylmethyl)chroman as a 1:1 mixture of diastereomers by 1H NMR.

Workup

  1. customwas prepared
  2. additionthe mixture was poured onto ice-cold saturated aqueous ammonium chloride
  3. extractionextracted with 150 mL of ether in several portions
  4. washThe combined organic layers were washed with four portions of water
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3bc5637e2de14d3bb7d3143a004e2325
Source dataset
uspto-grants-2010_09
Patent number
US07795272B2

Reaction notes

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