Pivaloyl chloride → HCID 23335544, compound

HRID 616959Notes

Reaction equation

HRID 616959 reaction equation
[O:1]1[CH2:16][CH:2]1[CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[C:8]([CH2:14][OH:15])[NH:9]2.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>N1C=CC=CC=1>[O:1]1[CH2:16][CH:2]1[CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[C:8]([CH2:14][O:15][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[NH:9]2

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 14044141{4-[(Oxiran-2-yl)methoxy]-1H-indol-2-yl}methanol

Product 1

HCID 23335544HCID 23335544, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

11.5 g. 4-(2,3-epoxypropoxy)-2-hydroxymethyl-indole (see U.S. Pat. No. 3,705,907) were dissolved in 100 ml. pyridine. To this solution were added dropwise, while cooling to 0° - 5° C., 6.5 g. (6.7 ml.) pivaloyl chloride. After an hour, the reaction mixture was poured on to ice and extracted with diethyl ether. The ethereal solution was successively washed with dilute sulfuric acid, aqueous sodium bicarbonate solution and water. After drying and treating with active charcoal, the solution was filtered and evaporated. The residue (13 g.; 82% of theory) crystallized upon triturating with diethyl ether/ligroin to give 4-(2,3-epoxypropoxy)-2-pivaloyloxymethyl-indole; m.p. 129° - 131° C.

Workup

  1. dissolution3,705,907) were dissolved in 100 ml
  2. additionTo this solution were added dropwise
  3. temperaturewhile cooling to 0° - 5° C.
  4. waitAfter an hour
  5. additionthe reaction mixture was poured on to ice
  6. extractionextracted with diethyl ether
  7. washThe ethereal solution was successively washed with dilute sulfuric acid, aqueous sodium bicarbonate solution and water
  8. customAfter drying
  9. additiontreating with active charcoal
  10. filtrationthe solution was filtered
  11. customevaporated
  12. customThe residue (13 g.; 82% of theory) crystallized
  13. customupon triturating with diethyl ether/ligroin

Sources & evidence

ORD record
ord-99aa38af99de4cc4826ff4c7279bc690
Source dataset
uspto-grants-1978_02
Patent number
US04076829

Reaction notes

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