Methyl iodide → HCID 12294713, compound

HRID 449424

Reaction equation

HRID 449424 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:11][O:12][C:13](=[O:21])[CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[CH3:22]I>O1CCCC1.O>[CH:15]1([CH:14]([CH3:22])[C:13]([O:12][CH3:11])=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 139743Cyclohexaneacetic acid, methyl esterHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 12294713HCID 12294713, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

1.0 M of Lithium hexamethyldisilazide in tetrahydrofuran (2.2 mL, 2.2 mmol) was added to a solution of methylcyclohexylacetate (0.30 g, 1.9 mmol) (Aldrich, Cat. #209600) in tetrahydrofuran (7.0 mL) at −78° C. The mixture was stirred at −78° C. for 1 h., then methyl iodide (0.14 mL, 2.3 mmol) was added. The mixture was allowed to warm slowly to r.t., and stirred at r.t. overnight. The mixture was diluted with water, and extracted with ethyl acetate (3×10 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-10%) to afford the desired product (0.30 g, 92%).

Workup

  1. temperatureto warm slowly to r.t.
  2. stirringstirred at r.t. overnight
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-10%)

Sources & evidence

ORD record
ord-1b000c91065e4ff0ae48a03224f8819a
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Linked notes

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