Sodium hydride → 8-fluoro-3,4-dihydro-2H-1,5-benzoxathiepine

HRID 548754Notes

Reaction equation

HRID 548754 reaction equation
[H-].[Na+].F[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[S:11][CH2:12][CH2:13][CH2:14][OH:15]>CN(C=O)C>[F:10][C:8]1[CH:7]=[CH:6][C:5]2[S:11][CH2:12][CH2:13][CH2:14][O:15][C:4]=2[CH:9]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 433923683-(2,4-Difluorophenyl)sulfanylpropan-1-ol

Product 1

HCID 576632148-fluoro-3,4-dihydro-2H-1,5-benzoxathiepineYield 29.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil) (177 mg, 4.42 mmol) was added to a solution of 3-[(2,4-difluorophenyl)thio]propan-1-ol (0.41 g, 2.01 mmol) in DMF (40 mL) and the mixture stirred at RT for 24 hours. The solvent was removed in vacuo and iced water (200 mL) added. The mixture was extracted into ethyl acetate and the organics washed with brine (40 mL), dried (MgSO4), filtered and reduced in vacuo to give a white solid which was chromatographed on silica, eluting with 0-10% ethyl acetate in isohexane, to give the desired compound as a colourless oil (110 mg).

Workup

  1. customThe solvent was removed in vacuo and iced water (200 mL)
  2. additionadded
  3. extractionThe mixture was extracted into ethyl acetate
  4. washthe organics washed with brine (40 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customto give a white solid which
  8. customwas chromatographed on silica
  9. washeluting with 0-10% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-bb2f8f483ed64533a82b93a0a91eecd2
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

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