4-Hydroxymethylpyridine → HCID 9838340, compound

HRID 234643Notes

Reaction equation

HRID 234643 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.C([Li])CCC.[C:14]12([C:24](Cl)=[O:25])[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2.C(=O)(O)[O-].[Na+]>C1COCC1.CCCCCC.O>[C:14]12([C:24]([O:8][CH2:7][C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)=[O:25])[CH2:21][CH:20]3[CH2:19][CH:18]([CH2:17][CH:16]([CH2:22]3)[CH2:15]1)[CH2:23]2

Participants

8

Reactant 4

HCID 114724-HydroxymethylpyridineHCID 989151-Adamantanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 178418339Butyllithium

Product 1

HCID 9838340HCID 9838340, compoundYield 35%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To 4-pyridylcarbinol (1.2 g, 11.0 mmol) in THF (40 ml) at -18° C. was added n-butyllithium (2.5 M, 4.2 ml, 10.5 mmol) in hexane dropwise with stirring. After 10 minutes a solution of 1-adamantanecarbonyl chloride (2.0 g, 10.0 mmol) in THF (10 ml) was added and stirring continued at room temperature for 30 minutes. The mixture was poured into water, basified with saturated aqueous sodium bicarbonate, and extracted with ether. The ether extracts were combined, dried (Na2CO3) and concentrated, Chromatography, on elution with petrol-ether-triethylamine 100:50:1, gave the title compound (0.95 g, 35%), which crystallised from 60-80 petrol, m.p. 57°-58° C., IR νmax 1730 cm-1 ; 1H-NMR(CDCl3) δ1.74 and 1.96 (12H, 2s, adamantyl CH2), 2.05 (3H, s, adamantyl CH), 5.12 (2H, s, OCH2), 7.24 (2H, d, J 5.7 Hz, Py 3 and 6H), 8.60 (2H, d, J 5.7 Hz, Py 2 and 6H). Anal. Calcd: C, 75.24; H, 7.80; N, 5.16. Found: C, 75.34; H, 7.92; N, 5.04%.

Workup

  1. stirringstirring
  2. extractionextracted with ether
  3. dry with materialdried (Na2CO3)
  4. concentrationconcentrated
  5. washChromatography, on elution with petrol-ether-triethylamine 100:50:1

Sources & evidence

ORD record
ord-07c8e932775d4abab4f6633a0fb99da3
Source dataset
uspto-grants-1997_01
Patent number
US05595995

Reaction notes

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