Diglycolamine → HCID 54245395, compound

HRID 974418Notes

Reaction equation

HRID 974418 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](=[O:20])[CH2:15][CH2:16][C:17]([OH:19])=O)[CH:5]=[CH:4][C:3]1=2.[OH:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][NH2:28]>ClCCl>[OH:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][NH:28][C:17](=[O:19])[CH2:16][CH2:15][C:14]([C:6]1[CH:5]=[CH:4][C:3]2[C:2]([CH3:1])([CH3:21])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]=2[CH:7]=1)=[O:20]

Participants

4

Reactant 2

HCID 13578DiglycolamineHCID 10469392HCID 10469392, compound

Product 1

HCID 54245395HCID 54245395, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 2.88 g (10 mmoles) of 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-oxo butyric acid, described in Example III, and 1.95 g (12 mmoles) of N,N'-carbonyl diimidazole in 50 cm3 of anhydrous dichloromethane is stirred for 2 hours at ambient temperature. The resulting solution is cooled to a temperature between +5° and +10° C. and 1.26 g (12 mmoles) of N-2-hydroxyethoxyethylamine are added. Stirring is continued for 3 hours while permitting the reaction mixture to return to ambient temperature. The reaction mixture is transferred to a separatory funnel and diluted to 100 cm3. After washing with 0.1N HCl and then with water, the dichloromethane phase is dried on sodium sulfate and then evaporated to dryness. The residue is purified by chromatography on silica 60 gel in a 40/25/25/10 dichloromethane/toluene/ethyl acetate/isopropanol eluant mixture. After evaporation and drying, there are obtained 2.5 g of N-(2-hydroxyethoxyethyl) 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-4-oxo butyramide in the form of a thick colorless oil kept out of contact with light.

Workup

  1. additionare added
  2. stirringStirring
  3. waitis continued for 3 hours
  4. customto return to ambient temperature
  5. customThe reaction mixture is transferred to a separatory funnel
  6. additiondiluted to 100 cm3
  7. washAfter washing with 0.1N HCl
  8. dry with materialwith water, the dichloromethane phase is dried on sodium sulfate
  9. customevaporated to dryness
  10. customThe residue is purified by chromatography on silica 60 gel in a 40/25/25/10 dichloromethane/toluene/ethyl acetate/isopropanol eluant mixture
  11. customAfter evaporation
  12. customdrying

Sources & evidence

ORD record
ord-32795dfe39794443b80d1b29944249f5
Source dataset
uspto-grants-1991_11
Patent number
US05068393

Reaction notes

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