Hexane → HCID 90051767, compound

HRID 2284741Notes

Reaction equation

HRID 2284741 reaction equation
[C:1]([C:3]([CH2:12][CH2:13][O:14][CH3:15])([CH2:8][CH2:9][O:10][CH3:11])[C:4]([O:6]C)=[O:5])#[N:2].[OH-].[Na+].CCCCCC.COC(C)(C)C>O1CCCC1>[C:1]([C:3]([CH2:8][CH2:9][O:10][CH3:11])([CH2:12][CH2:13][O:14][CH3:15])[C:4]([OH:6])=[O:5])#[N:2]

Participants

6

Reactant 4

HCID 8058HexaneHCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 11593730HCID 11593730, compound

Product 1

HCID 90051767HCID 90051767, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-cyano-4-methoxy-2-(2-methoxyethyl)butanoate (1.13 g) synthesized according to the method described in European Journal of Organic Chemistry, 2005, vol. 20, pp. 4313-4321 in tetrahydrofuran (10 mL), 1.0 mol/L aqueous sodium hydroxide (20 mL) was added at room temperature, and the mixture was stirred at the same temperature for 7 hours. To the reaction mixture, hexane and tert-butyl methyl ether were added. The aqueous layer was separated, and ethyl acetate and 1.0 mol/L aqueous hydrochloric acid were added. The organic layer was separated, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 2-cyano-4-methoxy-2-(2-methoxyethyl)butyric acid (G19, 957 mg).

Workup

  1. customThe aqueous layer was separated
  2. additionethyl acetate and 1.0 mol/L aqueous hydrochloric acid were added
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ccf1ed5cd66c40b8a482a08b51dbc3dc
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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