Acetic Acid → HCID 24875800, compound

HRID 564307Notes

Reaction equation

HRID 564307 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]2[C:16]3[C:17]([F:22])=[CH:18][CH:19]=[C:20]([F:21])[C:15]=3[O:14][CH2:13][CH:12]2[CH2:23]OS(C)(=O)=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Na+].[I-].C(O)(=O)C>COCCOC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]2[C:16]3[C:15](=[C:20]([F:21])[CH:19]=[CH:18][C:17]=3[F:22])[O:14][CH2:13][CH:12]2[CH3:23])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5238Sodium IodideHCID 72472590HCID 72472590, compound

Product 1

HCID 24875800HCID 24875800, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Methanesulfonic acid O-[4-(4-chloro-benzenesulfonyl)-5,8-difluoro-3,4-dihydro-2H-1-benzopyran-3-yl-methyl]ester (0.5 g, 1.1 mmole), NaI (0.83 g, 5.5 mmole) Zinc dust (0.71 g, 11 mole) and 0.1 mL acetic acid were refluxed in 15 mL ethylene glycol dimethyl ether for 6 hours. The solid was filtered and the filtrate was partitioned between 100 mL 0.1N Na2SO3 solution and 100 mL EtOAc. The organic layer was washed with 0.5N NaOH solution (2×50 ml), brine, dried over Na2SO4 and concentrated. The residue was recrystallized from EtOAc/Hexane to pure product (0.33 g, 83%) 1H NMR (400 MHz, CDCl3) 7.71 (d, J=8.8 Hz, 2H), 7.50 (d, J=8.8 Hz, 2H), 7.03 (m, 1H), 6.40 (m, 1H), 4.92 (dd, J=11.7 and 2.9 Hz, 1H), 4.21 (m, 2H), 3.02 (m, 1H), 1.07 (d, J=7.3 Hz, 3H).

Workup

  1. filtrationThe solid was filtered
  2. customthe filtrate was partitioned between 100 mL 0.1N Na2SO3 solution and 100 mL EtOAc
  3. washThe organic layer was washed with 0.5N NaOH solution (2×50 ml), brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was recrystallized from EtOAc/Hexane to pure product (0.33 g, 83%) 1H NMR (400 MHz, CDCl3) 7.71 (d, J=8.8 Hz, 2H), 7.50 (d, J=8.8 Hz, 2H), 7.03 (m, 1H), 6.40 (m, 1H), 4.92 (dd, J=11.7 and 2.9 Hz, 1H), 4.21 (m, 2H), 3.02 (m, 1H), 1.07 (d, J=7.3 Hz, 3H)

Sources & evidence

ORD record
ord-8c88ac888ca94218a27da31e6816a4bc
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

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