Imidazole → 1,2,3,6-Tetrahydrobenzylalcohol, tert-butyldimethylsilyl ether

HRID 32855Notes

Reaction equation

HRID 32855 reaction equation
[CH2:1]([OH:8])[CH:2]1[CH2:7][CH:6]=[CH:5][CH2:4][CH2:3]1.N1C=CN=C1.[CH3:14][C:15]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])[CH3:16]>CN(C=O)C.[Cl-].[Na+].O>[Si:18]([O:8][CH2:1][CH:2]1[CH2:3][CH2:4][CH:5]=[CH:6][CH2:7]1)([C:15]([CH3:17])([CH3:16])[CH3:14])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 155123-Cyclohexene-1-methanolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 112298861,2,3,6-Tetrahydrobenzylalcohol, tert-butyldimethylsilyl etherYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of 1,2,3,6-tetrahydrobenzylalcohol (1) (1.12 g, 10 mmol) and imidazole (1.36 g, 20 mmol) in DMF (10 mL) was added TBDMSCl (1.81 g, 12 mmol). After 20 hours, the mixture was treated with brine (100 mL) and the product was extracted with hexanes (3×80 mL). The combined organic layers were washed with brine (100 mL), dried over MgSO4 and evaporated in vacuo to give compound (2) (2.26 g, 100%) as colorless liquid. Rf0.29 (hexanes). 1H NMR (CDCl3) δ 5.65-5.64 (m, 2H), 3.48 (d, J=2.3 Hz, 1H), 3.45 (d, J=2.3 Hz, 1H), 2.08-2.00 (m, 3H), 1.82-1.66 (m, 3H), 1.32-1.19 (m, 1H), 0.89 (s, 9H), 0.04 (s, 6H); 13C NMR (CDCl3) δ 127.04, 126.23, 67.95, 36.34, 28.23, 25.97, 25.70, 25.33, 24.78, 18.38, −5.32.

Workup

  1. extractionthe product was extracted with hexanes (3×80 mL)
  2. washThe combined organic layers were washed with brine (100 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-396347309c7e45c5aa561df64ccbeaed
Source dataset
uspto-grants-2008_09
Patent number
US07427678B2

Reaction notes

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