Tetrahydrofuran → HCID 90238651, compound

HRID 1478772Notes

Reaction equation

HRID 1478772 reaction equation
[H-].[Na+].Br[CH2:4][CH:5]([O:9][CH2:10][CH3:11])[O:6][CH2:7][CH3:8].[O:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>>[CH2:7]([O:6][CH:5]([O:9][CH2:10][CH3:11])[CH2:4][O:12][C@@H:13]([C@@H:13]1[CH2:14][CH2:15][CH2:16][O:12]1)[CH2:14][CH:15]=[CH2:16])[CH3:8].[CH2:7]([O:6][CH:5]([O:9][CH2:10][CH3:11])[CH2:4][O:12][C@H:13]([C@@H:13]1[CH2:14][CH2:15][CH2:16][O:12]1)[CH2:14][CH:15]=[CH2:16])[CH3:8]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 2

HCID 90238651HCID 90238651, compoundHCID 90238674HCID 90238674, compound

Procedure

To a solution of crude (C94) (16.0 g, ≦1.112 mol) in tetrahydrofuran (600 mL) at 0° C. was added sodium hydride (60% in mineral oil, 13.5 g, 0.33 mol) portion-wise. After addition was complete, the reaction was allowed to warm to room temperature and stir at that temperature for 30 minutes. 2-Bromo-1,1-diethoxyethane (83 g, 0.33 mol) was added and the reaction was refluxed for 16 hours. The reaction mixture was cooled to room temperature and poured into ice-water (100 mL). The aqueous layer was washed with ethyl acetate (3×200 mL), and the organic phases were combined and washed with saturated aqueous sodium chloride solution (200 mL), dried over sodium sulfate, filtered and concentrated in vacuo. Silica gel chromatography (Gradient: 1% to 10% ethyl acetate in petroleum ether) provided (2S)-2-[(1R)-1-(2,2-diethoxyethoxyl)but-3-en-1-yl]tetrahydrofuran as the first eluting isomer and (2S)-2-[(1S)-1-(2,2-diethoxyethoxyl)but-3-en-1-yl]tetrahydrofuran as the second eluting isomer, both as yellow oils.

Workup

  1. additionAfter addition
  2. temperaturethe reaction was refluxed for 16 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. washThe aqueous layer was washed with ethyl acetate (3×200 mL)
  5. washwashed with saturated aqueous sodium chloride solution (200 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ec602b68340b422bbc3bb5651e07086c
Source dataset
uspto-grants-2016_08
Patent number
US09403846B2

Reaction notes

Loading…