2-Methyl-2-butanol → HCID 20510601, compound

HRID 1758192Notes

Reaction equation

HRID 1758192 reaction equation
[C:1](O)([CH2:4][CH3:5])([CH3:3])C.[OH:7][CH:8]([CH2:42][N:43]1[C:48]([CH3:50])([CH3:49])[CH2:47][CH:46]([OH:51])[CH2:45][C:44]1([CH3:53])[CH3:52])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH:28]([OH:41])[CH2:29][N:30]3[C:35]([CH3:37])([CH3:36])[CH2:34][CH:33]([OH:38])[CH2:32][C:31]3([CH3:40])[CH3:39])=[CH:22][CH:21]=2)([CH3:19])[CH3:18])=[CH:13][CH:12]=1.[CH2:54](Br)[CH2:55][CH2:56][CH3:57].C(O[CH2:63][CH3:64])(=O)C.C(N([CH2:70][CH3:71])CC)C>C(O)C.C1C=CC=CC=1>[CH2:54]([O:41][CH:28]([CH2:29][N:30]1[C:35]([CH3:36])([CH3:37])[CH2:34][CH:33]([O:38][CH2:70][CH2:71][CH2:63][CH3:64])[CH2:32][C:31]1([CH3:40])[CH3:39])[CH2:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([C:17]([C:14]2[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH:8]([O:7][CH2:3][CH2:1][CH2:4][CH3:5])[CH2:42][N:43]3[C:48]([CH3:50])([CH3:49])[CH2:47][CH:46]([O:51][CH2:3][CH2:1][CH2:4][CH3:5])[CH2:45][C:44]3([CH3:53])[CH3:52])=[CH:16][CH:15]=2)([CH3:19])[CH3:18])=[CH:25][CH:24]=1)[CH2:55][CH2:56][CH3:57]

Participants

8

Reactant 5

HCID 64052-Methyl-2-butanolHCID 8002Butyl bromideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 20510553HCID 20510553, compound

Product 1

HCID 20510601HCID 20510601, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

To 300 ml of t-pentyl alcohol were added potassium t-pentoxide (prepared from 5.0 g of metallic potassium) and 6.6 g of 2,2-bis{4-[2-hydroxy-3-(4-hydroxy-2,2,6,6-tetramethylpiperidino)propoxy]-phenyl}propane (obtained as described in Example 1); the mixture was refluxed for 2 hours. The reaction mixture was cooled to ambient temperature and there were added 10.0 g of n-butyl bromide. The mixture was heated at 50°-60° C. for 15 hours. After completion of the reaction, the reaction mixture was condensed by evaporation under reduced pressure and the residue was extracted with benzene. The extract was washed with water and dried over anhydrous potassium carbonate. The solvent was removed from the dried solution by evaporation under reduced pressure and the resulting residue was purified by column chromatography through silica gel eluted with a 2:5 by volume mixture of ethyl acetate and benzene. The desired Compound No. 30 was obtained in the form of a colourless viscous oil having an Rf value of 0.68 on thin-layer chromatography on silica gel developed with a 8:1:1:1 by volume mixture of ethyl acetate, benzene, ethanol and triethylamine.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureThe mixture was heated at 50°-60° C. for 15 hours
  3. customAfter completion of the reaction
  4. customcondensed
  5. customby evaporation under reduced pressure
  6. extractionthe residue was extracted with benzene
  7. washThe extract was washed with water
  8. dry with materialdried over anhydrous potassium carbonate
  9. customThe solvent was removed from the dried solution by evaporation under reduced pressure
  10. customthe resulting residue was purified by column chromatography through silica gel
  11. washeluted with a 2:5 by volume mixture of ethyl acetate and benzene
  12. custom30 was obtained in the form of a colourless viscous oil

Sources & evidence

ORD record
ord-25c7c46092184de58c380fc181596439
Source dataset
uspto-grants-1983_02
Patent number
US04371644

Reaction notes

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