Diethyl Ether → HCID 86707587, compound

HRID 2279976Notes

Reaction equation

HRID 2279976 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[C:19](OS(C(F)(F)F)(=O)=O)[CH:18]=[C:17]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[CH:31][CH:30]=3)[CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:43][O:44][CH2:45][CH2:46][O:47][CH2:48][O:49][CH2:50][CH2:51][CH2:52][C:53]1[CH:58]=[CH:57][C:56](B2OC(C)(C)C(C)(C)O2)=[CH:55][CH:54]=1.[OH-].[NH3+]N.CCOCC>O.C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[C:19]([C:56]3[CH:55]=[CH:54][C:53]([CH2:52][CH2:51][CH2:50][O:49][CH2:48][O:47][CH2:46][CH2:45][O:44][CH3:43])=[CH:58][CH:57]=3)[CH:18]=[C:17]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[CH:31][CH:30]=3)[CH:16]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 44558531Aminoammonium hydroxideHCID 86707581HCID 86707581, compoundHCID 86707586HCID 86707586, compound

Product 1

HCID 86707587HCID 86707587, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4.00 g (6.78 mmol) trifluoromethanesulfonic acid-4,4″-bis-benzyloxy-[1,1′;3′,1″]terphenyl-5′-yl ester, 2.37 g (6.78 mmol) 2-{4-[3-(2-methoxyethoxymethoxy)-propyl]-phenyl}-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane and 2.85 g (20 mmol) sodium metaborate-tetrahydrate are dissolved in 8 ml water and 20 ml THF. 97 mg (0.135 mmol) bis(triphenylphosphine)palladium(II)chlorid and 0.01 ml hydraziniumhydroxide are added and the mixture is heated at reflux for 5 h. MTB ether is added, the aqueous layer is separated and extracted three times with MTB ether. The combined organic layers are washed with sat. aq. sodium chloride solution and dried over sodium sulfate. The solvent is removed in vacuo and the residue is filtered through silica gel with dichloromethane/MTB ether (95:5), to give 4,4″-bis-benzyloxy-5′-(4-[3-(2-methoxy-ethoxymethoxy)-propyl]-phenyl)-[1,1′;3′,1″]terphenyl as a brown oil which is reacted in the next step without further purification.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 5 h
  3. customthe aqueous layer is separated
  4. extractionextracted three times with MTB ether
  5. washThe combined organic layers are washed with sat. aq. sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customThe solvent is removed in vacuo
  8. filtrationthe residue is filtered through silica gel with dichloromethane/MTB ether (95:5)

Sources & evidence

ORD record
ord-28925d3814774727a50ac8838a9280be
Source dataset
uspto-grants-2015_09
Patent number
US09133395B2

Reaction notes

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