Toluene → HCID 22723506, compound

HRID 1581830Notes

Reaction equation

HRID 1581830 reaction equation
[C:1]([C:3]([CH3:11])([CH3:10])[CH:4]([OH:9])[CH2:5][C:6]([OH:8])=[O:7])#[N:2].[C:12]1(C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([C:3]([CH3:11])([CH3:10])[CH:4]([OH:9])[CH2:5][C:6]([O:8][CH3:12])=[O:7])#[N:2]

Participants

7

Reactant 4

HCID 1140Toluene2×HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 22723509HCID 22723509, compound

Product 1

HCID 22723506HCID 22723506, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

R-N-(p-Hydroxybenzyl)phenylethylamine salt (8.42 g, 22.7 mmol) of optically active 4-cyano-3-hydroxy-4-methylpentanoic acid was dissolved in water (20 mL) and toluene (20 mL) was added. 2N Aqueous potassium carbonate solution (22.7 mL, 45.4 mmol) was gradually added dropwise with vigorous stirring. After stirring vigorously at room temperature for 30 min, the mixture was partitioned and an organic layer was removed. Then, toluene (20 mL) and tetrabutylammonium bromide (1.01 g, 3.42 mmol) were added and dimethyl sulfate (3.15 g, 25.0 mmol) was dropwise added with vigorous stirring. The reaction mixture was stirred at room temperature for 2 hr, and a toluene layer was separated and concentrated under reduced pressure to give optically active methyl 4-cyano-3-hydroxy-4-methylpentanoate (3.62 g). The yield was 93.4% relative to optically active 4-cyano-3-hydroxy-4-methylpentanoic acid.

Workup

  1. customthe mixture was partitioned
  2. customan organic layer was removed
  3. stirringThe reaction mixture was stirred at room temperature for 2 hr
  4. customa toluene layer was separated
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c43ca55c8e124154a970f4d7474e790d
Source dataset
uspto-grants-2004_05
Patent number
US06730803B2

Reaction notes

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