Triethylsilane → Isobutyl 1-methyl-4-(2-methoxyethoxy)cyclohexanecarboxylate

HRID 2060015Notes

Reaction equation

HRID 2060015 reaction equation
[CH3:1][C:2]1([C:9]([O:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:10])[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.C([Si](C)(C)O[CH2:22][CH2:23][O:24][CH3:25])(C)(C)C.C([SiH](CC)CC)C>C(#N)C>[CH3:1][C:2]1([C:9]([O:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:10])[CH2:3][CH2:4][CH:5]([O:8][CH2:22][CH2:23][O:24][CH3:25])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 11805534tert-Butyl-(2-methoxyethoxy)dimethylsilaneHCID 594441322-Methylpropyl 1-methyl-4-oxocyclohexanecarboxylate

Product 1

HCID 59444164Isobutyl 1-methyl-4-(2-methoxyethoxy)cyclohexanecarboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of isobutyl 1-methyl-4-oxocycylohexanecarboxylate (D67, 12.7 g, 59.8 mmol), t-butyl dimethyl 2-methoxyethoxy silane (11.4 g, 59.9 mmol), and anhydrous ferric chloride (250 mg, 1.541 mmol) in acetonitrile (150 mL) at 0° C. was treated with triethylsilane (12 mL, 75 mmol). The mixture was stirred for 1 h at room temperature, then partitioned between saturated sodium bicarbonate and dichloromethane, and the organic layer was dried and evaporated to give isobutyl 1-methyl-4-(2-methoxyethoxy)cyclohexanecarboxylate (27 g, 49.6 mmol, 83% yield) as a cis/trans mixture containing one equivalent of t-butyldimethyl triethyl siloxane.

Workup

  1. custompartitioned between saturated sodium bicarbonate and dichloromethane
  2. customthe organic layer was dried
  3. customevaporated

Sources & evidence

ORD record
ord-0cae6e7f8e3942ab8dd7af051fecf07a
Source dataset
uspto-grants-2012_10
Patent number
US08278328B2

Reaction notes

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