Ethyl Acetate → HCID 68527740, compound

HRID 2386197Notes

Reaction equation

HRID 2386197 reaction equation
[Si]([O:8][CH:9]([C:24]1[O:25][C:26]([I:29])=[CH:27][N:28]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>O1CCCC1>[I:29][C:26]1[O:25][C:24]([CH:9]([OH:8])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=2)=[N:28][CH:27]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 68527986HCID 68527986, compound

Product 1

HCID 68527740HCID 68527740, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(1-(tert-Butyl dimethylsilyloxy)-7-(3-methoxyphenyl)heptyl)-5-iodooxazole (0.088 g, 0.166 mmol) was dissolved in tetrahydrofuran (2 mL) under an atmosphere of argon with stirring and 1 M tetrabutylammonium fluoride (in tetrahydrofuran) (0.199 mL, 0.199 mmol) was added. The reaction was allowed to proceed over 90 minutes before dilution with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The solvent was removed in vacuo and the desired product was purified as an oily white solid in 88% yield (0.061 g) using flash column chromatography with silica (0-30% ethyl acetate:hexanes gradient mobile phase): 1H NMR (500 MHz, CDCl3) δ 7.17-7.20 (m, 1H), 7.07 (s, 1H), 6.76 (d, J=7.5 Hz), 6.72 (m, 2H), 4.77 (q, 1H), 3.79 (s, 3H), 3.24 (bs, 1H), 2.57 (t, 2H), 1.80-1.93 (m, 2H), 1.58-1.62 (m, 2H), 1.43-1.48 (m, 1H), 1.30-1.42 (m, 5H); 13C NMR (150 MHz, CDCl3) δ 170.52, 159.48, 144.32, 135.05, 129.11, 120.79, 114.13, 110.80, 110.74, 86.84, 67.48, 55.07, 35.89, 35.21, 31.16, 29.03 (2 C), 24.84; HRMS (ES+) mile calc'd for [M+H]+ C17H23INO3: 416.0717. found 416.0699.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was removed in vacuo
  4. customthe desired product was purified as an oily white solid in 88% yield (0.061 g)

Sources & evidence

ORD record
ord-bace993a1d204e25b611ab18d6358e97
Source dataset
uspto-grants-2012_09
Patent number
US08268817B2

Reaction notes

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