Acetic Acid → HCID 11243484, compound

HRID 495146Notes

Reaction equation

HRID 495146 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9](=[O:11])[CH:8]=[C:7]([O:12][CH2:13][CH2:14][CH2:15][O:16]C3CCCCO3)[C:6]=2[CH:23]=1.CC(O)=O.C1COCC1>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9](=[O:11])[CH:8]=[C:7]([O:12][CH2:13][CH2:14][CH2:15][OH:16])[C:6]=2[CH:23]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 57683735HCID 57683735, compound

Product 1

HCID 11243484HCID 11243484, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Bromo-4-[3-(tetrahydro-pyran-2-yloxy)-propoxy]-1-benzopyran-2-one (0.893 mmol, 0.342 g) is treated with 5 mL of 4:2:1 HOAc:THF:H2O and is heated to 45° C. for 1 hr. The solvent is removed under reduced pressure and the residue is purified by HPLC to afford the title compound (105.8 mg, 60%); 1H NMR (DMSO-d6, 300 MHz) δ 7.90 (1H, d, J=2.5 Hz), 7.82 (1H, dd, J=2.25, 8.75 Hz), 7.39 (1H, d, J=8.75 Hz), 5.96 (1H, s), 4.29 (2H, t, J=6.25 Hz), 3.61 (2H, t, J=6 Hz), 1.97 (2H, m); MS (ESI, Pos.) calcd for C12H11BrO4 m/z [M+H]=299.0, found 299.1.

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue is purified by HPLC

Sources & evidence

ORD record
ord-4c5d31bda20b4e01ac34ca977b7578bd
Source dataset
uspto-grants-2009_05
Patent number
US07538233B2

Reaction notes

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