Imidazole → 3-(Tert-butyldimethylsilyloxymethyl)benzonitrile

HRID 1866893Notes

Reaction equation

HRID 1866893 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].N1C=CN=C1.[CH3:16][C:17]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])[CH3:18]>C(Cl)Cl.CN(C1C=CN=CC=1)C.O>[Si:20]([O:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7])([C:17]([CH3:19])([CH3:18])[CH3:16])([CH3:22])[CH3:21]

Participants

7

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 27346773-(Hydroxymethyl)benzonitrile

Product 1

HCID 220502983-(Tert-butyldimethylsilyloxymethyl)benzonitrileYield 99%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of 3-hydroxymethyl benzonitrile (4.95 g, 37 mmol) in CH2Cl2 (47 mL) was added imidazole (5.1 g, 74 mmol), DMAP (0.45 g, 3.7 mmol), and TBSCl (6.2 g, 41 mmol), and the reaction mixture was stirred for 12 h. The reaction mixture was diluted with water, and the aqueous layer was extracted with CH2Cl2 (3×150 mL). The combined organics were washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure to provide 3-(tert-butyldimethylsilyloxymethyl)-benzonitrile (9-1 g, 99%) as a clear oil: 1H NMR (300 MHz, CDCl3) δ 7.51 (s, 1H), 7.42 (d, J=6 Hz, 1H), 7.35-7.28 (m, 1H), 4.75 (s, 2H), 0.94 (s, 9H), 0.11 (s, 6H).

Workup

  1. extractionthe aqueous layer was extracted with CH2Cl2 (3×150 mL)
  2. washThe combined organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-803bc9b966e24ad2b280d5a876c72807
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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