Sodium borohydride → 3-Pyridinemethanol, 4-iodo-2-methoxy-6-(trimethylsilyl)-

HRID 2086335Notes

Reaction equation

HRID 2086335 reaction equation
[BH4-].[Na+].[I:3][C:4]1[CH:9]=[C:8]([Si:10]([CH3:13])([CH3:12])[CH3:11])[N:7]=[C:6]([O:14][CH3:15])[C:5]=1[CH:16]=[O:17]>CCO>[I:3][C:4]1[CH:9]=[C:8]([Si:10]([CH3:11])([CH3:13])[CH3:12])[N:7]=[C:6]([O:14][CH3:15])[C:5]=1[CH2:16][OH:17]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 109365704-Iodo-2-methoxy-6-trimethylsilanyl-pyridine-3-carbaldehyde

Product 1

HCID 120443583-Pyridinemethanol, 4-iodo-2-methoxy-6-(trimethylsilyl)-Yield 78.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of NaBH4 (1.1 g, 26.4 mmol) in EtOH (100 mL) at −40° C. was slowly added a solution of 4-iodo-2-methoxy-6-trimethylsilanyl-3-pyridinecarboxaldehyde 1 (31.8 g, 94.9 mmol) in EtOH (50 mL). See Josien, H.; Ko, S.-B.; Bom, D.; Curran, D. P. Chem. Eur. J., 67 (1998). After stirring for 1 h, the reaction mixture was carefully quenched with brine and then extracted 3 times with Et2O. The combined organic extracts were dried over MgSO4. The solvent was removed under reduced pressure and the residue purified by flash chromatography (gradient hexane to hexane-EtOAc 91:9) to afford 2a (25.1 g, 78% yield) as a clear oil. 1H NMR (300 MHz, CDCl3) δ0.28 (s, 9H), 2.5 (bs, 1H), 4.01 (s, 3H), 4.8 (s, 2H), 7.5 (s, 1H); 13C NMR (75 MHz, CDCl3) δ−1.99, 53.78, 65.32, 11.65, 125.34, 133.19, 160.9, 165.81; IR (film, NaCl, cm−1) 3485, 2960, 1580, 1450, 1039, 839; LRMS (70 eV, EI) m/z (rel int %) 337 (M+), 322 (100), 306, 194, 180, 73. HRMS m/z calcd for C10H16NO2SiI (M+) 336.9996, found 337.000.

Workup

  1. customthe reaction mixture was carefully quenched with brine
  2. extractionextracted 3 times with Et2O
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customthe residue purified by flash chromatography (gradient hexane to hexane-EtOAc 91:9)

Sources & evidence

ORD record
ord-e569f1554503429eaac84fba9f2f5010
Source dataset
uspto-grants-2004_04
Patent number
US06723853B2

Reaction notes

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