Pivaloyl chloride → [4-(2-Oxiranylmethoxy)-1H-indol-6-yl]methyl 2,2-dimethylpropanoate

HRID 261805Notes

Reaction equation

HRID 261805 reaction equation
[O:1]1[CH2:16][CH:2]1[CH2:3][O:4][C:5]1[CH:13]=[C:12]([CH2:14][OH:15])[CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][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]=[C:12]([CH2:14][O:15][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][NH:9]2

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 23335534{4-[(Oxiran-2-yl)methoxy]-1H-indol-6-yl}methanol

Product 1

HCID 23335539[4-(2-Oxiranylmethoxy)-1H-indol-6-yl]methyl 2,2-dimethylpropanoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8.7 g. 4-(2,3-epoxypropoxy)-6-hydroxymethyl-indole (cf. the preparation of the starting material in Example 15) were dissolved in 50 ml. anhydrous pyridine. To this solution were added dropwise, while stirring and cooling to 5°-10° C., 5 ml. pivalic acid chloride, 1.5-2 hours after the ending of the addition, the reaction mixture was poured into ice water. The aqueous phase was extracted 3 or 4 times with diethyl ether. The ethereal extract was successively washed with 1 N sulfuric acid, a saturated aqueous solution of sodium bicarbonate and water, then dried, treated with active charcoal and fullers' earth and subsequently evaporated. The crude 4-(2,3-epoxypropoxy)-6-pivaloyloxymethyl-indole thus obtained (12.5 g.; about 100% of theory) was further reacted without further purification.

Workup

  1. customthe preparation of the starting material in Example 15)
  2. dissolutionwere dissolved in 50 ml
  3. additionTo this solution were added dropwise
  4. temperaturecooling to 5°-10° C.
  5. extractionThe aqueous phase was extracted 3 or 4 times with diethyl ether
  6. extractionThe ethereal extract
  7. washwas successively washed with 1 N sulfuric acid
  8. dry with materiala saturated aqueous solution of sodium bicarbonate and water, then dried
  9. additiontreated with active charcoal and fullers' earth
  10. customsubsequently evaporated

Sources & evidence

ORD record
ord-54b5c95b09414783a3ba227e2f099f87
Source dataset
uspto-grants-1979_05
Patent number
US04152446

Reaction notes

Loading…