1,2-Dimethoxyethane → HCID 20386207, compound

HRID 46587Notes

Reaction equation

HRID 46587 reaction equation
[OH:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.COCCOC.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>N1C=CC=CC=1>[C:17]([O:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 62493Pivaloyl chlorideHCID 757711-Hydroxybenzotriazole

Product 1

HCID 20386207HCID 20386207, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
21 °C

Procedure

To a mixture of 1-hydroxybenzotriazole (30.6 g), 1,2-dimethoxyethane (150 ml), and pyridine (16 g), there was added, while stirring at 21° C., pivaloyl chloride (24.1 g) during 0.75 hr. During the addition, the temperature of the reaction mixture was raised to 34° C. by the heat evolved. The reaction was then heated externally at 88° C. for an additional 0.5 hr. period then cooled, washed with water, and extracted with 1,1,2-trichlorotrifluoroethane. The extract was dried and stripped of solvent and the residue was column chromatographed on neutral alumina in benzene solvent. The product, 1-benzotriazolyl pivalate, was obtained as a brown oil after removal of the benzene solvent. The elemental analysis was as follows:

Workup

  1. additionwas added
  2. additionDuring the addition
  3. temperaturethe temperature of the reaction mixture was raised to 34° C. by the heat
  4. temperatureThe reaction was then heated externally at 88° C. for an additional 0.5 hr
  5. temperatureperiod then cooled
  6. washwashed with water
  7. extractionextracted with 1,1,2-trichlorotrifluoroethane
  8. customThe extract was dried
  9. customchromatographed on neutral alumina in benzene solvent

Sources & evidence

ORD record
ord-eaa9b99f42a742828294ac68c1b66f0f
Source dataset
uspto-grants-1979_11
Patent number
US04174285

Reaction notes

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