Hexane → HCID 86743801, compound

HRID 1165067Notes

Reaction equation

HRID 1165067 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:7]([OH:12])(=[O:11])[C:8]([CH3:10])=[CH2:9].[C:13]1([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][C:28]=2[O:37]CCO)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[O:23]CCO.CCCCCC>CC#N.C1COCC1>[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:7]([OH:12])(=[O:11])[C:8]([CH3:10])=[CH2:9].[C:27]1([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][C:14]=2[O:23][CH:1]([OH:6])[CH3:2])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][C:28]=1[O:37][CH:7]([OH:11])[CH3:8]

Participants

5

Reactant 2

HCID 8058HexaneHCID 86743802HCID 86743802, compound

Product 1

HCID 86743801HCID 86743801, compoundYield 142.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

BMPDMS (260 mg), TASHF2 (100 microliters, 0.1 M. in CH3CH) and THF (125 mL) were added to a dry 250 mL 3-necked round-bottomed flask equipped with a magnetic stirrer, a thermocouple, a reflux condenser and a nitrogen bubbler and the mixture was cooled to 0° C. A solution of (±)-2,2'-((1,1'-binaphthalene)-2,2'-diylbis(oxy))-bis(ethanol) dimethacrylate (2.5 g, 4.9 mmole) and TASHF2 (100 μL, 0.1 M. in CH3CN) in THF (125 mL) were added dropwise (0.5 mL/min) to the solution in the 250 mL flask to give a yellow mixture. This mixture was stirred overnight at 0° C. and then condensed. Hexane was added, and the polymer which precipitated was dried to give 1.91 g of a white powdery solid.

Workup

  1. customequipped with a magnetic stirrer
  2. customto give a yellow mixture
  3. customcondensed
  4. customthe polymer which precipitated
  5. customwas dried

Sources & evidence

ORD record
ord-8607c71f2759460e9a4add84050f23d7
Source dataset
uspto-grants-1990_03
Patent number
US04906713

Reaction notes

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