Acetic Anhydride → HCID 68877740, compound

HRID 1354004Notes

Reaction equation

HRID 1354004 reaction equation
[I:1][C:2]1[CH:3]=[C:4](/[CH:11]=[CH:12]\[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15](O)[CH:14]=2)[CH:5]=[C:6]([I:10])[C:7]=1[O:8][CH3:9].[C:22](OC(=O)C)(=[O:24])[CH3:23]>N1C=CC=CC=1>[I:1][C:2]1[CH:3]=[C:4](/[CH:11]=[CH:12]\[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([C:22](=[O:24])[CH3:23])[CH:14]=2)[CH:5]=[C:6]([I:10])[C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 21103234HCID 21103234, compound

Product 1

HCID 68877740HCID 68877740, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

An appropriate phenol 22a (0.45 g) was dissolved in pyridine (3 mL)-acetic anhydride (170 μL) and stirred for 2 hrs. The mixture was concentrated under reduced pressure from toluene (3×10 mL). The residue was diluted with EtOAc (30 mL), washed successively with water (10 mL), NaHCO3 (10% aq. sol., 10 mL), dried, and the solution filtered and concentrated. The acetate was further purified by flash chromatography on silica using 1:24 hexane-EtOAc:hexane as eluent to afford acetate 22c (0.20 g, 41%) as a colorless solid:recrystallized from hexane mp 121–122° C.; 1H-NMR (300 MHz, CDCl3) δ 2.29 (s, 3 H), 3.83 (s, 3 H), 3.85 (s, 3 H), 6.29 (d, 1 H, J=12 Hz), 6.48 (d, 1 H, J=12 Hz), 6.85 (d, 1 H, J=8.7 Hz), 6.93 (d, 1 H, J=2.43), 7.06 (d, 1 H, J=1.5), 7.09 (d, 1 H, J=2.4 Hz) and 7.67 (s, 2 H); 13C-NMR (125 MHz, CDCl3) δ 20.66, 55.94, 60.72, 90.11, 112.16, 123.25, 125.41, 127.47, 128.85, 130.64, 137.10, 139.54, 139.89, 150.69, 157.67 and 168.79; HRMS calcd for C19H20I2O5582.9479 [M+CH3OH]+, found 582.9482; Anal. calcd for C18H16I2O4 C, 39.30; H, 2.93. Found C, 39.30; H, 3.13%.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure from toluene (3×10 mL)
  2. additionThe residue was diluted with EtOAc (30 mL)
  3. washwashed successively with water (10 mL), NaHCO3 (10% aq. sol., 10 mL)
  4. customdried
  5. filtrationthe solution filtered
  6. concentrationconcentrated
  7. customThe acetate was further purified by flash chromatography on silica using 1:24 hexane-EtOAc

Sources & evidence

ORD record
ord-64e0a400f947404cb640b80fdad99aed
Source dataset
uspto-grants-2007_05
Patent number
US07223747B2

Reaction notes

Loading…