Sodium hydride → HCID 70978651, compound

HRID 1852159Notes

Reaction equation

HRID 1852159 reaction equation
[H-].[Na+].[CH3:3][C:4]1([OH:8])[CH2:7][O:6][CH2:5]1.[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][C:16](=O)[O:17]C1C=CC=CN=1>C1COCC1.CCOC(C)=O>[C:16](=[O:17])([O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][N:9]=1)[O:8][C:4]1([CH3:3])[CH2:7][O:6][CH2:5]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 2757370Carbonic acid di-2-pyridyl esterHCID 229187883-Methyloxetan-3-ol

Product 1

HCID 70978651HCID 70978651, compoundYield 28.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium hydride, 60% in mineral oil (0.817 g, 20.43 mmol) in THF (55 mL) was added 3-methyloxetan-3-ol (1.5 g, 17.03 mmol) at 0° C. After stirring 30 min, the solution was transferred to a solution of di(pyridin-2-yl)carbonate (3.68 g, 17.03 mmol) in THF (55 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-methyloxetan-3-yl pyridin-2-yl carbonate (1.00 g, 28.1% yield) as an oil. 1H NMR (400 MHz, CHLOROFORM-d) d 8.52-8.35 (m, 1H), 7.84 (ddd, J=8.1, 7.3, 2.1 Hz, 1H), 7.31-7.27 (m, 1H), 7.15 (dt, J=8.1, 0.8 Hz, 1H), 4.97-4.85 (m, 2H), 4.54 (d, J=8.0 Hz, 2H), 1.86 (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-d5af15986ced49c2bb53cd7cefcdb517
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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