Tetrahydrofuran → HCID 69601051, compound

HRID 2215084Notes

Reaction equation

HRID 2215084 reaction equation
O[CH2:2][C@H:3]1[CH2:7][S:6][C:5](=[O:8])[N:4]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].CC(OI1(OC(C)=O)(OC(C)=O)O[C:31](=O)[C:30]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]1=2)=O.[H-].[Na+].C1C[O:47][CH2:46][CH2:45]1>C(Cl)Cl>[O:8]=[C:5]1[N:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C@@H:3](/[CH:2]=[CH:45]/[C:46](=[O:47])[CH2:31][C:30]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:7][S:6]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 159087TriacetoxyperiodinaneHCID 69601136HCID 69601136, compound

Product 1

HCID 69601051HCID 69601051, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-6 (0.56 g, 2.0 mmol) in 10 mL CH2Cl2 was added Dess Martin periodinane (0.98 g, 2.3 mmol) in portions and the resulting solution was stirred for 2 hours. The solution was concentrated in vacuo, to which toluene was added and concentrated thrice to remove acetic acid. The concentrate was then filtered through celite with CH2Cl2 and concentrated in vacuo. The crude product was then diluted in 5 mL of THF and added to a solution of the Wittig reagent dimethyl 2-oxo-3-phenylpropylphosphonate (0.75 g, 3.1 mmol) and 60% sodium hydride (0.12 g, 2.9 mmol) in 5 mL of THF at 0° C. which was premixed for half an hour. The reaction mixture was stirred for 15 minutes at the initial temperature and was allowed to warm up to room temperature for one hour and was stored at 4° C. overnight. The reaction was then quenched with saturated aqueous ammonium chloride solution and was extracted with ethyl acetate. The organic phases were then combined, sequentially washed with H2O, brine and dried over Na2SO4. After filtration and concentration in vacuo, the compound was purified by flash chromatography using 50% ethyl acetate/hexanes to yield 400 mg of 3-7 as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.40–7.21 (m, 5H), 6.75 (dd, 1H), 6.31 (d, 1H), 4.14 (q, 2H), 3.89 (s, 2H), 3.57–3.45 (m, 3H), 3.01 (dd, 1H), 2.75 (m, 1H), 2.31 (t, 2H), 1.64–1.22 (m, 8H), 1.28 (t, 3H); MS (+ESI): m/z 404.2 (M+1)+.

Workup

  1. concentrationThe solution was concentrated in vacuo, to which toluene
  2. additionwas added
  3. concentrationconcentrated thrice
  4. customto remove acetic acid
  5. filtrationThe concentrate was then filtered through celite with CH2Cl2
  6. concentrationconcentrated in vacuo
  7. additionThe crude product was then diluted in 5 mL of THF
  8. additionwas premixed for half an hour
  9. stirringThe reaction mixture was stirred for 15 minutes at the initial temperature
  10. waitwas stored at 4° C. overnight
  11. customThe reaction was then quenched with saturated aqueous ammonium chloride solution
  12. extractionwas extracted with ethyl acetate
  13. washsequentially washed with H2O, brine
  14. dry with materialdried over Na2SO4
  15. filtrationAfter filtration and concentration in vacuo
  16. customthe compound was purified by flash chromatography

Sources & evidence

ORD record
ord-bf4301873837409fb410153bf9ec02c4
Source dataset
uspto-grants-2006_09
Patent number
US07109223B2

Reaction notes

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