Pyridine → HCID 86647318, compound

HRID 1848427Notes

Reaction equation

HRID 1848427 reaction equation
[OH:1][CH2:2][CH:3]1[C:12]2[C:7](=[C:8]3[CH2:15][O:14][C:13](=[O:16])[C:9]3=[CH:10][CH:11]=2)[CH2:6][CH2:5][O:4]1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.N1C=CC=CC=1>C(Cl)Cl>[O:16]=[C:13]1[C:9]2[C:8](=[C:7]3[C:12](=[CH:11][CH:10]=2)[CH:3]([CH2:2][O:1][S:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=2)(=[O:25])=[O:24])[O:4][CH2:5][CH2:6]3)[CH2:15][O:14]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 68432696HCID 68432696, compound

Product 1

HCID 86647318HCID 86647318, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(Hydroxymethyl)-8,9-dihydro-1H-furo[3,4-f]isochromen-3(6H)-one, in DCM (10 mL) was treated with p-Toluenesulfonyl chloride (0.40 g, 2.3 mmol); to the mixture was added pyridine (2 mL) and the resulting mixture stirred at room temperature for 12 h. TLC (hexanes/EtOAc=1/0.5) and LC indicated the consumption of starting material and formation of the desired product. Dichloromethane was added to the reaction mixture and it was washed with NaCl, water and dried over Na2SO4, filtered and concentrated to dryness, absorbed onto silica gel and was then subjected to purification over silica gel; the title compound was isolated with the solvent system of hexanes/EtOAc (1/0.5). 1H-NMR (400 MHz, CDCl3) δ ppm 7.781 (d, J=8 Hz, 1H), 7.727 (d, J=8 Hz, 1H), 7.367 (d, J=8 Hz, 1H), 7.257 (d, J=8.5 Hz, 1H), 7.206 (d, J=8 Hz, 1H), 5.253 (s, 2H), 5.110 (s, 1H), 4.481-4.452 (m, 2H), 4.419-4.385 (m, 2H), 4.196-4.153 (m, 2H), 2.495 (s, 3H).

Workup

  1. customthe consumption of starting material and formation of the desired product
  2. additionDichloromethane was added to the reaction mixture and it
  3. washwas washed with NaCl, water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customabsorbed onto silica gel
  8. customwas then subjected to purification over silica gel

Sources & evidence

ORD record
ord-a17b75e4dc0048cd9e9351bbbbff55f5
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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