Tetrahydrofuran → HCID 54123206, compound

HRID 1590932Notes

Reaction equation

HRID 1590932 reaction equation
CN(CC1C=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=1)C.[CH2:20]([CH:24]([C:40]([O:42][CH:43]1[CH2:48][C:47]([CH3:50])([CH3:49])[N:46]([O:51][CH3:52])[C:45]([CH3:54])([CH3:53])[CH2:44]1)=[O:41])[C:25]([O:27][CH:28]1[CH2:33][C:32]([CH3:35])([CH3:34])[N:31]([O:36][CH3:37])[C:30]([CH3:39])([CH3:38])[CH2:29]1)=[O:26])[CH2:21][CH2:22][CH3:23].[NH2-].[Li+].O1C[CH2:60][CH2:59][CH2:58]1>C(OCC)(=O)C.O>[C:16]([C:7]1[CH:6]=[C:59]([CH:58]=[C:9]([C:11]([CH3:13])([CH3:14])[CH3:12])[C:8]=1[OH:15])[CH2:60][C:24]([CH2:20][CH2:21][CH2:22][CH3:23])([C:40]([O:42][CH:43]1[CH2:44][C:45]([CH3:53])([CH3:54])[N:46]([O:51][CH3:52])[C:47]([CH3:50])([CH3:49])[CH2:48]1)=[O:41])[C:25]([O:27][CH:28]1[CH2:29][C:30]([CH3:39])([CH3:38])[N:31]([O:36][CH3:37])[C:32]([CH3:34])([CH3:35])[CH2:33]1)=[O:26])([CH3:17])([CH3:18])[CH3:19]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24532Lithium amideHCID 66609Phenol, 4-[(dimethylamino)methyl]-2,6-bis(1,1-dimethylethyl)-HCID 54237698HCID 54237698, compound

Product 1

HCID 54123206HCID 54123206, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 11.9 g (45.2 mmol) of N,N-dimethyl-3,5-di-t-butyl-4-hydroxybenzylamine, 18.8 g (37.7 mmol) of di-(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) n-butylmalonate, 173 mg of lithium amide, and 100 ml of tetrahydrofuran is refluxed for 90 minutes. The reaction mixture is diluted with ethyl acetate (350 ml). The organic solution is washed with 1N HCl (2×100 ml), water (2×250 ml), and saturated NaHCO3 solution (250 ml), then dried over magnesium sulfate and evaporated to obtain a brown oil. Crystallization from 9:1 methanol:water affords 14.9 g (55% yield) of a white solid (mp 111°-13° C.).

Workup

  1. temperatureis refluxed for 90 minutes
  2. washThe organic solution is washed with 1N HCl (2×100 ml), water (2×250 ml), and saturated NaHCO3 solution (250 ml)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto obtain a brown oil
  6. customCrystallization from 9:1 methanol

Sources & evidence

ORD record
ord-c61e77ba238d42819b7f42a2fd3bbc97
Source dataset
uspto-grants-1993_04
Patent number
US05204473

Reaction notes

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