2-tert-Butyldimethylsilyloxymethyl-6-(1-methoxy-1-methylethyl)pyridine → 2-Hydroxymethyl-6-(1-methoxy-1-methylethyl)pyridine

HRID 876997Notes

Reaction equation

HRID 876997 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([O:19][CH3:20])([CH3:18])[CH3:17])[N:11]=1)(C(C)(C)C)(C)C>CC(O)=O.C1COCC1.O>[OH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([O:19][CH3:20])([CH3:17])[CH3:18])[N:11]=1

Participants

5

Reactant 1

HCID 667184232-tert-Butyldimethylsilyloxymethyl-6-(1-methoxy-1-methylethyl)pyridine

Product 1

HCID 667184342-Hydroxymethyl-6-(1-methoxy-1-methylethyl)pyridineYield 100.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-tert-butyldimethylsilyloxymethyl-6-(1-methoxy-1-methylethyl)pyridine (1.20 g, 4.08 mmol) in AcOH (45 mL), THF (15 mL) and H2O (15 mL) was stirred for 48 h at room temperature. The solvent was removed in vacuo, the residue was partitioned between DCM and sat aq NaHCO3, the organic portion was separated, dried (MgSO4), filtered and evaporated to give the title compound (740 mg, 100%) as a colourless oil; NMR δH (400 MHz, CDCl3) 7.70-7.66 (1H, m), 7.48-7.45 (1H, m), 7.07-7.04 (1H, m), 4.74 (2H, d, J 5.0 Hz), 4.14 (1H, t, J 5.0 Hz), 3.18 (3H, s), 1.57 (6H, s).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between DCM
  3. customthe organic portion was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-2f3bdbc127854edea92cf9e0d1f248b6
Source dataset
uspto-grants-2015_03
Patent number
US08987279B2

Reaction notes

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