Dimethyl Sulfide → HCID 18694150, compound

HRID 1870993Notes

Reaction equation

HRID 1870993 reaction equation
S(C)C.ClCCl.[F:7][C:8]1[CH:9]=[C:10]([N+:21]([O-:23])=[O:22])[C:11]2[O:16][CH:15]([C:17](O)=[O:18])[CH2:14][CH2:13][C:12]=2[CH:20]=1>O1CCCC1>[F:7][C:8]1[CH:9]=[C:10]([N+:21]([O-:23])=[O:22])[C:11]2[O:16][CH:15]([CH2:17][OH:18])[CH2:14][CH2:13][C:12]=2[CH:20]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 6344DichloromethaneHCID 18694183HCID 18694183, compound

Product 1

HCID 18694150HCID 18694150, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1M solution of (CH3)2S.BH3 in dichloromethane (0.28 mol) was added dropwise to a mixture of intermediate 13-b (0.25 mol) in tetrahydrofuran (800 ml), stirred under N2 flow. About 60 ml of the solvent was removed by distillation. The reaction mixture was stirred and refluxed for 2 h. The mixture was cooled, decomposed with CH3OH (20 ml), poured out into H2O/NaOH and this mixture was extracted with CH2Cl2. The separated organic layer was washed with water, dried (MgSO4), filtered and the solvent was evaporated, yielding 59 g of (±)-6-fluoro-3,4-dihydro-8-nitro-2H-1-benzopyran-2-methanol (104% crude residue) (interm. 14-b).

Workup

  1. customAbout 60 ml of the solvent was removed by distillation
  2. stirringThe reaction mixture was stirred
  3. temperaturerefluxed for 2 h
  4. temperatureThe mixture was cooled
  5. additionpoured out into H2O/NaOH
  6. extractionthis mixture was extracted with CH2Cl2
  7. washThe separated organic layer was washed with water
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-1b497905716d408b8d2a1d36cfd15df5
Source dataset
uspto-grants-2000_08
Patent number
US06100268

Reaction notes

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