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Dimethylformamide → HCID 21470422, compound

HRID 2294748
Notes
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Reaction equation

HRID 2294748 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21])(=O)=O)=CC=1.[OH:23][C:24]1[CH:25]=[C:26]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:28][CH:29]=1.CN(C)C=O.[H-].[Na+]>O>[CH2:21]([O:23][C:24]1[CH:25]=[C:26]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:28][CH:29]=1)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=[CH2:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 9881286HCID 9881286, compoundHCID 11141895HCID 11141895, compound

Product 1

HCID 21470422HCID 21470422, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

The above-prepared 6.20 g (19.1 mM) of 10-undecenyl p-toluenesulfonate, 4.62 g (19.1 mM) of ethyl p-hydroxybiphenylcarboxylate and 6 ml of dimethylformamide (DMF) were mixed and sufficiently stirred. To the mixture, 0.77 g (19.3 mM) of 60% -sodium hydride was added, followed by heat-refluxing for 7 hours. After the reaction, the reaction mixture was subjected to distilling-off of DMF and addition of water, followed by extraction with ether to obtain an extract. The extract was dried with anhydrous sodium sulfate, followed by distilling-off of ether and purification by column chromatography (eluent: methylene chloride) to obtain 6.46 g (16.4 mM) of ethyl p-(10-undecenyl)oxybiphenylcarboxylate (Yield: 86%).

Workup

  1. temperatureby heat-refluxing for 7 hours
  2. customAfter the reaction
  3. extractionfollowed by extraction with ether
  4. customto obtain an extract
  5. dry with materialThe extract was dried with anhydrous sodium sulfate
  6. distillationfollowed by distilling-off of ether and purification by column chromatography (eluent: methylene chloride)

Sources & evidence

ORD record
ord-a722a0376f494d4bb7e8612bfb28baf0
Source dataset
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05690858

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes