Hexane → HCID 18942524, compound

HRID 1806923Notes

Reaction equation

HRID 1806923 reaction equation
[OH:1][CH2:2][CH2:3][C:4]([CH3:9])([CH3:8])[C:5]([OH:7])=[O:6].[CH3:10]CCCCC.C[Si](C=[N+]=[N-])(C)C>C(OCC)C.CO>[CH3:10][O:6][C:5](=[O:7])[C:4]([CH3:9])([CH3:8])[CH2:3][CH2:2][OH:1]

Participants

6

Reactant 3

HCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 138845934-Hydroxy-2,2-dimethylbutanoic acid

Product 1

HCID 18942524HCID 18942524, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Step B To the mixture of 4-hydroxy-2,2-dimethyl-butanoic acid (2.2 g, 16.6 mmol) in ethyl ether (16 mL) and methanol (24 mL) at 0° C. was added a hexane solution (2.0 M) of trimethylsilyldiazomethane (Aldrich) (12.5 mL, 25 mmol). The reaction mixture was stirred at 0° C. for 1 h. The solvents were evaporated. The residue was taken up in ethyl acetate, washed with diluted aqueous HCl solution, saturated aqueous NaHCO3 solution, brine, dried over MgSO4, and concentrated to give 4-hydroxy-2,2-dimethyl-butyric acid methyl ester as a colorless oil (1.5 g, 62%).

Workup

  1. customThe solvents were evaporated
  2. washwashed with diluted aqueous HCl solution, saturated aqueous NaHCO3 solution, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c8ac715d6853432fb75e03bc6bd4bd8a
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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