Pivaloyl chloride → HCID 23335544, compound

HRID 903913Notes

Reaction equation

HRID 903913 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-f75cd2f430d34df4a710f80205c1bd6f
Source dataset
uspto-grants-1980_10
Patent number
US04229464

Reaction notes

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