Imidazole → Ethyl 4-(tert-butyldimethylsilyloxy)-2-ethylcyclopentanecarboxylate

HRID 1969805Notes

Reaction equation

HRID 1969805 reaction equation
[CH2:1]([CH:3]1[CH2:7][CH:6]([OH:8])[CH2:5][CH:4]1[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:2].[CH3:14][C:15]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])[CH3:16].N1C=CN=C1.CCCCCCC>CN(C=O)C>[Si:18]([O:8][CH:6]1[CH2:5][CH:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:3]([CH2:1][CH3:2])[CH2:7]1)([C:15]([CH3:17])([CH3:16])[CH3:14])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8900HeptaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 58557073HCID 58557073, compound

Product 1

HCID 58557197Ethyl 4-(tert-butyldimethylsilyloxy)-2-ethylcyclopentanecarboxylateYield 98.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 2-ethyl-4-hydroxycyclopentanecarboxylate (10.0 g, 53.7 mmol) in DMF (18 mL) was added TBDMS-Cl (9.72 g, 64.5 mmol) and imidazole (9.15 g, 134 mmol). The reaction mixture was stirred at ambient temperature for about 3 h. Heptane (50 mL) was added to the reaction and the layers were separated. The bottom layer was extracted with heptane (2×30 mL). The combined organic extracts were washed with water (2×30 mL), brine (30 mL), dried over anhydrous MgSO4, filtered and concd to give ethyl 4-(tert-butyldimethylsilyloxy)-2-ethylcyclopentanecarboxylate (15.87 g, 52.8 mmol, 98%) as a colorless oil; 1H NMR (400 MHz, CDCl3) δ 4.13 (m, 3H), 2.79 (m, 1H), 2.09 (m, 1H), 1.99 (m, 3H), 1.50-1.24 (m, 6H), 0.89 (m, 12H), 0.05 (s, 6H).

Workup

  1. customthe layers were separated
  2. extractionThe bottom layer was extracted with heptane (2×30 mL)
  3. washThe combined organic extracts were washed with water (2×30 mL), brine (30 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-db8044d5988a4a2b953b88a3e7d3281a
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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