Tetrahydrofuran → HCID 86710477, compound

HRID 1484533Notes

Reaction equation

HRID 1484533 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[C:12]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)(=[O:14])[CH3:13].[OH-:21].[Na+].[CH2:23]1[CH2:27][O:26][CH2:25][CH2:24]1>O>[CH2:1]([O:21][C:8]1[CH:7]=[C:6]([O:26][CH2:25][C:24]2[CH:23]=[CH:27][CH:11]=[CH:10][CH:9]=2)[CH:11]=[CH:10][C:9]=1[C:12]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)([OH:14])[CH3:13])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 8058HexaneHCID 95893-AcetylpyridineHCID 14798Sodium HydroxideHCID 178418339Butyllithium

Product 1

HCID 86710477HCID 86710477, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-78 °C

Procedure

1.6 M n-butyllithium solution in hexane (14.9 ml; 23.8 mmol; 1.1 eq) is added dropwise to a solution of compound (12) (8 g; 21.7 mmol; 1.0 eq) in 300 ml of anhydrous THF cooled to −78° C. The solution is stirred for 1 hour at −78° C. and then 3-acetylpyridine (2.6 ml; 23.8 mmol; 1.1 eq) is added dropwise. The solution is stirred for 3 hours at −78° C., then for 15 hours at room temperature, and then 100 ml of water and 50 ml of 2 M aqueous sodium hydroxide solution are added. After extraction with ethyl acetate (2×150 ml), the organic phases are combined, dried over MgSO4 and concentrated under reduced pressure. The oil obtained is purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate: 4:6) to lead to a mixture of compound (16) and 3-acetylpyridine (6.7 g; 66% by mass of compound (16); 50%) obtained as a yellow oil.

Workup

  1. stirringThe solution is stirred for 3 hours at −78° C.
  2. waitfor 15 hours at room temperature
  3. extractionAfter extraction with ethyl acetate (2×150 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe oil obtained
  7. customis purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate: 4:6)
  8. additionto lead to a mixture of compound (16) and 3-acetylpyridine (6.7 g; 66% by mass of compound (16); 50%)
  9. customobtained as a yellow oil

Sources & evidence

ORD record
ord-29847ec9a6834349b61bfe64786ef169
Source dataset
uspto-grants-2016_08
Patent number
US09422261B2

Reaction notes

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