1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 44477924, compound

HRID 1805742Notes

Reaction equation

HRID 1805742 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([C:25]2[CH:26]=[CH:27][C:28]3[C:33]([CH:34]=2)=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:13]=[C:14]([CH2:16][O:17][Si](C(C)(C)C)(C)C)[CH:15]=1)(C(C)(C)C)(C)C.[C:35](Cl)([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)([C:44]1[CH:51]=[CH:50][C:47]([O:48][CH3:49])=[CH:46][CH:45]=1)[C:36]1[CH:43]=[CH:42][C:39]([O:40][CH3:41])=[CH:38][CH:37]=1>C(Cl)(Cl)Cl>[OH:17][CH2:16][C:14]1[CH:13]=[C:12]([C:25]2[C:26]3[C:31](=[CH:32][CH:33]=[CH:28][CH:27]=3)[CH:30]=[CH:29][CH:34]=2)[CH:11]=[C:10]([CH2:9][O:8][C:35]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)([C:44]2[CH:51]=[CH:50][C:47]([O:48][CH3:49])=[CH:46][CH:45]=2)[C:36]2[CH:43]=[CH:42][C:39]([O:40][CH3:41])=[CH:38][CH:37]=2)[CH:15]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 67381530HCID 67381530, compound

Product 1

HCID 44477924HCID 44477924, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

10.3 ml of pyrizine was added to dissolve 0.5448 g of Compound (6) in an Ar atmosphere, and 0.909 g (2.68 mmol, 1.3 eq) of DMTrCl was added. This was agitated for 18 hours in an Ar atmosphere. After extraction with chloroform, the organic layer was washed with H2O, sat. NaHCO3 aq and sat. NaCl aq, and dried by addition of anhydrous NaSO4. The solvent was distilled off under reduced pressure, and 0.4293 g (0.75 mmol, 37%) of Compound (7) was isolated by silica gel chromatography (chloroform only→chloroform:methanol=15:1).

Workup

  1. addition10.3 ml of pyrizine was added
  2. additionwas added
  3. extractionAfter extraction with chloroform
  4. washthe organic layer was washed with H2O, sat. NaHCO3 aq and sat. NaCl aq
  5. dry with materialdried by addition of anhydrous NaSO4
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cacb9555174d4792a2f80fd0c4a172d6
Source dataset
uspto-grants-2013_01
Patent number
US08354515B2

Reaction notes

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