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

HRID 2183493ノート

反応式

HRID 2183493 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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%).

後処理

  1. customto yield

出典と根拠

ORDレコード
ord-e7ab6a179a474464b0422f9fdeb6c6e9
出典データセット
uspto-grants-2005_05
特許番号
US06900209B2

反応ノート

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