1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 87378883, compound

HRID 1805744Notes

Reaction equation

HRID 1805744 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([C:25]2[CH:26]=[CH:27][C:28]3[CH:29]=[CH:30][C:31]4[C:36]([C:37]=3[CH:38]=2)=[CH:35][CH:34]=[CH:33][CH:32]=4)[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:39](Cl)([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)([C:48]1[CH:55]=[CH:54][C:51]([O:52][CH3:53])=[CH:50][CH:49]=1)[C:40]1[CH:47]=[CH:46][C:43]([O:44][CH3:45])=[CH:42][CH:41]=1>CO>[OH:17][CH2:16][C:14]1[CH:13]=[C:12]([C:25]2[C:38]3[CH:29]=[CH:30][C:31]4[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:37]=3[CH:28]=[CH:27][CH:26]=2)[CH:11]=[C:10]([CH2:9][O:8][C:39]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)([C:48]2[CH:55]=[CH:54][C:51]([O:52][CH3:53])=[CH:50][CH:49]=2)[C:40]2[CH:47]=[CH:46][C:43]([O:44][CH3:45])=[CH:42][CH:41]=2)[CH:15]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 87378695HCID 87378695, compound

Product 1

HCID 87378883HCID 87378883, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

14.5 ml of pyrizine was added to dissolve 0.932 g of Compound (10) in an Ar atmosphere, and 1.27 g (3.77 mmol, 1.3 eq) of DMTrCl were 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 0.3473 g (0.56 mmol, 3-step 23%) of Compound (11) was isolated by silica gel chromatography (chloroform only→chloroform:methanol=100:1).

Workup

  1. addition14.5 ml of pyrizine was added
  2. additionwere 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 0.3473 g (0.56 mmol, 3-step 23%) of Compound (11)
  7. customwas isolated by silica gel chromatography (chloroform only→chloroform

Sources & evidence

ORD record
ord-e3cd29ea956844b89651ef1f6689d082
Source dataset
uspto-grants-2013_01
Patent number
US08354515B2

Reaction notes

Loading…