Sodium hydride → 2-(Tricyclo[3.3.1.13,7]dec-1-ylmethoxy)-4-iodo-pyridine

HRID 336586

Reaction equation

HRID 336586 reaction equation
[C:1]12([CH2:11][OH:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.F[C:14]1[CH:19]=[C:18]([I:20])[CH:17]=[CH:16][N:15]=1.[H-].[Na+]>O1CCCC1>[C:1]12([CH2:11][O:12][C:14]3[CH:19]=[C:18]([I:20])[CH:17]=[CH:16][N:15]=3)[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 70235702-Fluoro-4-iodopyridine

Product 1

HCID 866812602-(Tricyclo[3.3.1.13,7]dec-1-ylmethoxy)-4-iodo-pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Adamantanemethanol (0.820 g) and 2-fluoro-4-iodopyridine (0.22 g) in tetrahydrofuran (5 mL) was treated with sodium hydride (60% in mineral oil) (0.057) at room temperature for 6 hours. The reaction was quenched with ice-water and extracted with ethyl acetate (3×10 mL). The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by preparative TLC, eluting with petroleum ether/ethyl acetate (20/1) to provide the title compound.

Workup

  1. customThe reaction was quenched with ice-water
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC
  7. washeluting with petroleum ether/ethyl acetate (20/1)

Sources & evidence

ORD record
ord-4a19718923514227b8eb3231a09b9fe0
Source dataset
uspto-grants-2014_11
Patent number
US08889675B2

Linked notes

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