Sodium hydride → HCID 90409320, compound

HRID 869128Notes

Reaction equation

HRID 869128 reaction equation
[H-].[Na+].[O:3]1[CH2:6][CH:5]([OH:7])[CH2:4]1.Cl[C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16]>C1COCC1>[N+:15]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:9]=1[O:7][CH:5]1[CH2:6][O:3][CH2:4]1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27357814-Chloro-3-nitropyridineHCID 9942117Oxetan-3-ol

Product 1

HCID 90409320HCID 90409320, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

NaH (164.0 mg, 4.100 mmol) was added portionwise to a stirred solution of oxetan-3-ol (280.4 mg, 3.785 mmol) in THF (10.00 mL) to form a white suspension. The reaction mixture was stirred at ambient temperature for 10 mins then was added dropwise to a suspension of 4-chloro-3-nitro-pyridine (500 mg, 3.154 mmol) in THF (3 mL). The reaction mixture was stirred at ambient temperature for 1 hour. The reaction was quenched with water (20 mL) and partitioned with ethyl acetate (3×20 mL). The combined organics were washed with brine, dried (MgSO4), filtered and evaporated to dryness to afford the desired product as a beige solid (499 mg, 81%). LC-MS (M+H)+ 198.1; 1H NMR (500 MHz, DMSO-d6) δ 9.06 (s, 1H), 8.66 (d, J=5.9 Hz, 1H), 7.09 (d, J=5.9 Hz, 1H), 5.60 (tt, J=6.0, 4.7 Hz, 1H), 4.99 (ddd, J=7.9, 6.0, 1.1 Hz, 2H), 4.61 (ddd, J=7.7, 4.7, 1.1 Hz, 2H).

Workup

  1. customto form a white suspension
  2. stirringThe reaction mixture was stirred at ambient temperature for 1 hour
  3. customThe reaction was quenched with water (20 mL)
  4. custompartitioned with ethyl acetate (3×20 mL)
  5. washThe combined organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-a58b5da33e444518a0e5d4e9846f875b
Source dataset
uspto-grants-2015_03
Patent number
US08969360B2

Reaction notes

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