Sodium hydride → Carbonic acid, 2-pyridinyl tetrahydro-3-methyl-3-furanyl ester

HRID 1852163Notes

Reaction equation

HRID 1852163 reaction equation
[H-].[Na+].[CH3:3][C:4]1([OH:9])[CH2:8][CH2:7][O:6][CH2:5]1.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][C:17](=O)[O:18]C1C=CC=CN=1>C1COCC1.CCOC(C)=O>[C:17](=[O:18])([O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][N:10]=1)[O:9][C:4]1([CH3:3])[CH2:8][CH2:7][O:6][CH2:5]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 2757370Carbonic acid di-2-pyridyl esterHCID 97937103-METHYLTETRAHYDROFURAN-3-OL

Product 1

HCID 71004905Carbonic acid, 2-pyridinyl tetrahydro-3-methyl-3-furanyl esterYield 38.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium hydride, 60% in mineral oil (185 mg, 4.63 mmol) in THF (20 mL) was added 3-methyltetrahydrofuran-3-ol (394 mg, 3.86 mmol) at 0° C. After stirring 30 min, the solution was transferred to a solution of di(pyridin-2-yl)carbonate (834 mg, 3.86 mmol) in THF (20 mL) through a cannula. The formed slurry was stirred at 0° C. for 30 min. The slurry was warmed to rt and stirred for 2 h. The reaction was diluted with EtOAc, washed with brine, dried over MgSO4, filtered, concentrated to give a residue that was purified by Biotage (5-40% EtOAc:Hex) to afford the desired product 3-methyltetrahydrofuran-3-yl pyridin-2-yl carbonate (334 mg, 38.8% yield) as an oil. 1H NMR (400 MHz, CHLOROFORM-d) δ 8.48-8.29 (m, 1H), 7.91-7.73 (m, 1H), 7.29-7.25 (m, 1H), 7.16-7.12 (m, 1H), 4.23 (d, J=10.3 Hz, 1H), 4.02 (td, J=8.5, 7.2 Hz, 1H), 3.95 (td, J=8.4, 4.5 Hz, 1H), 3.76 (d, J=10.3 Hz, 1H), 2.58-2.47 (m, 1H), 2.11-2.02 (m, 1H), 1.76 (s, 3H).

Workup

  1. stirringThe formed slurry was stirred at 0° C. for 30 min
  2. stirringstirred for 2 h
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue that
  8. customwas purified by Biotage (5-40% EtOAc:Hex)

Sources & evidence

ORD record
ord-15c650da636f4106a3b3c80e1ed1f009
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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