Diisobutylaluminum hydride → HCID 67455467, compound

HRID 1846353Notes

Reaction equation

HRID 1846353 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13](OC)=[O:14])=[CH:11][N:10]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[N:10]=[CH:11][C:12]([CH2:13][OH:14])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 86659815HCID 86659815, compound

Product 1

HCID 67455467HCID 67455467, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 6-((tetrahydro-2H-pyran-2-yloxy)methyl)nicotinate (1.5 g, 6.0 mmol) was dissolved in THF (30 mL) and cooled to 0° C. under nitrogen. DIBAL-H (1.0 M in THF, 21 mL, 21 mmol) was added dropwise, via a syringe over 5 min, and stirred for 90 min. The reaction mixture was warmed to room temperature, and quenched with water (25 mL), followed by saturated NH4Cl (10 mL). After stirring for 10 minutes, the mixture was basified with solid KOH, extracted with CH2Cl2 (2×100 mL), washed with brine (100 mL), dried (MgSO4), filtered, and concentrated, to afford (6-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-3-yl)methanol as a yellow oil (1.3 g, 97%).

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. customquenched with water (25 mL)
  3. stirringAfter stirring for 10 minutes
  4. extractionextracted with CH2Cl2 (2×100 mL)
  5. washwashed with brine (100 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4545ca5de4224c3ea43261da245d74c6
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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