Dimethylformamide → 5-(tert-Butyldimethylsilyloxymethyl)-2-(hydroxymethyl)pyridine

HRID 2183493Notes

Reaction equation

HRID 2183493 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[CH:4][N:3]=1.[Li]CCCC.CN([CH:25]=[O:26])C.[BH4-].[Na+]>CCOCC>[Si:10]([O:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:25][OH:26])=[N:3][CH:4]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 4311764Sodium borohydrideHCID 6425754Pyridine, 2-bromo-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-HCID 178418339Butyllithium

Product 1

HCID 224732225-(tert-Butyldimethylsilyloxymethyl)-2-(hydroxymethyl)pyridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The reaction was carried out as described in Example 1, Step 3 using 2-bromo-5-(tert-butyldimethylsilyloxymethyl)pyridine (12 g, 39.7 mmol), BuLi (37 ml of a 1.6 M solution in hexanes, 59.6 mmol) DMF (9.2 ml, 0.12 mol) and NaBH4 (1.5 g, 39.7 mmol) to yield, after column chromatography on silica using Et2O as eluent, the title alcohol (6.66 g, 66%).

Workup

  1. customto yield

Sources & evidence

ORD record
ord-e7ab6a179a474464b0422f9fdeb6c6e9
Source dataset
uspto-grants-2005_05
Patent number
US06900209B2

Reaction notes

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