1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 44477982, compound

HRID 1805746Notes

Reaction equation

HRID 1805746 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:39]4=[C:40]5[C:31]([CH:32]=[CH:33][CH:34]=[C:35]5[CH:36]=[CH:37][C:38]=24)=[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:41](Cl)([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)([C:50]1[CH:57]=[CH:56][C:53]([O:54][CH3:55])=[CH:52][CH:51]=1)[C:42]1[CH:49]=[CH:48][C:45]([O:46][CH3:47])=[CH:44][CH:43]=1>CO>[OH:8][CH2:9][C:10]1[CH:11]=[C:12]([C:25]2[C:38]3[C:39]4=[C:40]5[C:35](=[CH:36][CH:37]=3)[CH:34]=[CH:33][CH:32]=[C:31]5[CH:30]=[CH:29][C:28]4=[CH:27][CH:26]=2)[CH:13]=[C:14]([CH2:16][O:17][C:41]([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)([C:50]2[CH:57]=[CH:56][C:53]([O:54][CH3:55])=[CH:52][CH:51]=2)[C:42]2[CH:49]=[CH:48][C:45]([O:46][CH3:47])=[CH:44][CH:43]=2)[CH:15]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 44477925HCID 44477925, compound

Product 1

HCID 44477982HCID 44477982, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

14.5 ml of pyrizine were added to dissolve 0.932 g of Compound (14) in an Ar atmosphere, and 1.27 g (3.77 mmol, 1.3 eq) of DMTrCl was added. This was agitated for 27 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 0.4632 g (0.72 mmol, 3-step 30%) of Compound (14) was isolated by silica gel chromatography (chloroform only→chloroform:methanol=100:1).

Workup

  1. addition14.5 ml of pyrizine were 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, and 0.4632 g (0.72 mmol, 3-step 30%) of Compound (14)
  7. customwas isolated by silica gel chromatography (chloroform only→chloroform

Sources & evidence

ORD record
ord-7220a38e3a8440f7ba517e7c0d4c60e3
Source dataset
uspto-grants-2013_01
Patent number
US08354515B2

Reaction notes

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