Pyridine → HCID 86647318, compound

HRID 1474356Notes

Reaction equation

HRID 1474356 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 6344DichloromethaneSolvent2×

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. Reaction mixture was treated with dichloromethane and washed with NaCl, water and dried over Na2SO4, filtered and concentrated to dryness, absorbed into silica gel and was then subjected for purification over silica gel; (3-oxo-3,6,8,9-tetrahydro-1H-furo[3,4-f]isochromen-6-yl)methyl-4-methylbenzenesulfonate 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. customReaction mixture
  3. washwashed with NaCl, water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customabsorbed into silica gel
  8. customwas then subjected for purification over silica gel

Sources & evidence

ORD record
ord-a6f13c51de1e488b9629e9f0c5b9009c
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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