p-Toluenesulfonic acid → HCID 18694189, compound

HRID 1870996Notes

Reaction equation

HRID 1870996 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:20])[C:5]2[O:10][CH:9]([CH2:11][O:12][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][O:14]3)[CH2:8][CH2:7][C:6]=2[CH:19]=1.CO[CH:23]1[CH2:27][CH2:26][CH:25](OC)O1.CC1C=CC(S(O)(=O)=O)=CC=1>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([N:20]2[CH:23]=[CH:27][CH:26]=[CH:25]2)[C:5]2[O:10][CH:9]([CH2:11][O:12][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][O:14]3)[CH2:8][CH2:7][C:6]=2[CH:19]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 790982,5-DimethoxytetrahydrofuranHCID 18694173HCID 18694173, compound

Product 1

HCID 18694189HCID 18694189, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of intermediate 16-b (0.036 mol), 2,5-dimethoxytetrahydrofuran (0.22 mol) and PTSA (catalytic quantity) in DMF (140 ml) was stirred for 90 min at 100° C. The solvent was evaporated. The residue was dissolved in CH2Cl2. The organic solution was washed once with water, dried (MgSO4), filtered and the solvent was evaporated The residue was purified by column chromatography over silica gel (eluent: CH2Cl2). The pure fractions were collected and the solvent was evaporated, yielding 6.6 g (55.3%) of (±)-6-fluoro-3,4-dihydro-8-(1H-pyrrol-1-yl)-2-[[(tetrahydro-2H-pyran-2-yl)oxy]-methyl]-2H-1-benzopyran (interm. 17-b).

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washThe organic solution was washed once with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated The residue
  7. customwas purified by column chromatography over silica gel (eluent: CH2Cl2)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d07efba51ea747209282cf40a16ac689
Source dataset
uspto-grants-2000_08
Patent number
US06100268

Reaction notes

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