2-(Trimethylsilyl)ethanol → 3-Oxo-cyclohexanecarboxylic acid 2-trimethylsilanyl-ethyl ester

HRID 132098Notes

Reaction equation

HRID 132098 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([OH:10])=[O:9])[CH2:3]1.[CH3:11][Si:12]([CH3:17])([CH3:16])[CH2:13][CH2:14]O.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.C(Cl)Cl.Cl>[CH3:11][Si:12]([CH3:17])([CH3:16])[CH2:13][CH2:14][O:9][C:8]([CH:4]1[CH2:5][CH2:6][CH2:7][C:2](=[O:1])[CH2:3]1)=[O:10]

Participants

7

Reactant 3

HCID 180132-(Trimethylsilyl)ethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27602523-Oxocyclohexane-1-carboxylic acid

Product 1

HCID 597337803-Oxo-cyclohexanecarboxylic acid 2-trimethylsilanyl-ethyl esterYield 100%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

3-oxo-cyclohexanecarboxylic acid (2.00 g, 14.1 mmol), 2-trimethylsilylethanol (2.5 mL, 17.4 mmol), 4-dimethylaminopyridine (148 mg, 1.21 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.44 g, 17.9 mmol) in methylene chloride (14 mL) was stirred for 18 h. The solution was diluted with 10% aqueous hydrochloric acid and extracted with methylene chloride. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated to yield 3.41 g (100% yield) of 3-oxo-cyclohexanecarboxylic acid 2-trimethylsilanyl-ethyl ester as a clear oil.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f6e6a92550cd4ae5845340c05523d8a4
Source dataset
uspto-grants-2008_06
Patent number
US07385085B2

Reaction notes

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