Diethylamine → HCID 21501146, compound

HRID 1729781Notes

Reaction equation

HRID 1729781 reaction equation
[OH:1][CH:2]([CH2:5][CH2:6][CH2:7][CH:8]([OH:19])[CH2:9][CH2:10][CH2:11][CH:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:13])[CH:3]=[CH2:4].[CH2:20]([NH:22][CH2:23][CH3:24])[CH3:21]>C1C=CC=CC=1.CCOCC.[O-2].[O-2].[Mn+4]>[CH2:20]([N:22]([CH2:23][CH3:24])[CH2:4][CH2:3][C:2]1([OH:1])[CH2:5][CH2:6][CH2:7][CH:8]([CH2:9][CH2:10][CH2:11][CH:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:13])[O:19]1)[CH3:21]

Participants

6

Reactant 2

HCID 8021DiethylamineHCID 21501105HCID 21501105, compound

Product 1

HCID 21501146HCID 21501146, compound

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 241BenzeneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

41.3 G. of 3,7-dihydroxy-11-tertiarybutoxy-dodec-1ene produced in Example 121 was dissolved in benzene solution and added to a slurry of 320 g. of activated manganese dioxide in 1600 ml. of benzene containing 120 ml. of diethylamine. The reaction mixture was stirred at room temperature for 20 hours and filtered free of solids. Removal of the solvents in vacuo gave a pale brown oil. The oil was dissolved in ether and extracted with aqueous 1N hydrochloric acid. Sodium hydroxide was added to the acid extract. Extraction into ether and evaporation of the solvent affords 2-[2'-diethylaminoethyl]-6-[4-t-butoxypentyl]-2-tetrahydropyranol.

Workup

  1. additionadded to a slurry of 320 g
  2. filtrationfiltered free of solids
  3. customRemoval of the solvents in vacuo
  4. customgave a pale brown oil
  5. extractionextracted with aqueous 1N hydrochloric acid
  6. additionSodium hydroxide was added to the acid
  7. extractionextract
  8. extractionExtraction
  9. custominto ether and evaporation of the solvent

Sources & evidence

ORD record
ord-ee1d4648ceb74d5da57d8e2a28f52f30
Source dataset
uspto-grants-1976_11
Patent number
US03989724

Reaction notes

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