Water → HCID 66803133, compound

HRID 341542Notes

Reaction equation

HRID 341542 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.CC(C)([O-])C.[K+].Cl[C:15]1[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][N:16]=1.O>C1COCC1>[O:1]1[CH2:6][CH2:5][CH:4]([O:7][C:15]2[N:16]=[CH:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][CH:25]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 74956Tetrahydro-4H-pyran-4-olHCID 2799611Ethyl 6-chloronicotinateHCID 23665647Potassium tert-butoxide

Product 1

HCID 66803133HCID 66803133, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Oxan-4-ol (0.302 g, 2.96 mmol) was dissolved in THF (5 mL) and cooled to 0 C under nitrogen. Potassium tert-butoxide (0.332 g, 2.96 mmol) was added and the mixture stirred for 5 min. Ethyl 6-chloronicotinate (0.500 g, 2.69 mmol) was added, the mixture was warmed to room temperature and stirred for 3 h. Water (5 mL) was added and the mixture extracted with EtOAc (2×10 mL). The organic layers were dried over sodium sulfate and concentrated under vacuum. The residue was purified by FCC, eluting with a gradient of 5-20% EtOAc in heptane to afford the title compound as a colourless oil (0.239 g, 35%). 1H NMR (250 MHZ, CDCl3) δ ppm 8.80 (1H, dd), 8.14 (1H, m), 6.73 (1H, dd), 5.25 (1H, m), 4.39 (2H, dq), 3.96 (2H, m), 3.60 (2H, m), 2.05 (2H, m), 1.81 (2H, m) and 1.40 (3H, dt).

Workup

  1. temperaturecooled to 0 C under nitrogen
  2. stirringstirred for 3 h
  3. extractionthe mixture extracted with EtOAc (2×10 mL)
  4. dry with materialThe organic layers were dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by FCC
  7. washeluting with a gradient of 5-20% EtOAc in heptane

Sources & evidence

ORD record
ord-98456a59da4549e2a6c1afece76cf791
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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