1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 22873060, compound

HRID 1781571Notes

Reaction equation

HRID 1781571 reaction equation
[C:1]([C:6]1[C:7](=[O:21])[NH:8][C:9](=[O:20])[N:10]([CH:19]=1)[C@@H:11]1[O:18][C@H:15]([CH2:16][OH:17])[C@@H:13]([OH:14])[CH2:12]1)#[C:2][CH2:3][CH2:4][CH3:5].[CH3:22][O:23][C:24]1[CH:45]=[CH:44][C:27]([C:28](Cl)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)=[CH:26][CH:25]=1>N1C=CC=CC=1>[CH3:36][O:35][C:32]1[CH:31]=[CH:30][C:29]([C:28]([O:17][CH2:16][C@H:15]2[O:18][C@@H:11]([N:10]3[CH:19]=[C:6]([C:1]#[C:2][CH2:3][CH2:4][CH3:5])[C:7](=[O:21])[NH:8][C:9]3=[O:20])[CH2:12][C@@H:13]2[OH:14])([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:27]2[CH:44]=[CH:45][C:24]([O:23][CH3:22])=[CH:25][CH:26]=2)=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 11493075HCID 11493075, compound

Product 1

HCID 22873060HCID 22873060, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 20.4 g (69.3 mmol) of 5-(1-pentynyl)-2'-deoxyuridine in 300 mL of dry pyridine was added 22.8 g of 4,4'-dimethoxytrityl chloride. The reaction was stirred for 17 h at room temperature and then concentrated. The residue was taken up in CH2Cl2 and washed twice with 0.5% aqueous NaHCO3, dried (Na2SO4), filtered, and concentrated. Purification of the crude product by column chromatography afforded 21.9 g (52.9% yield) of product.

Workup

  1. concentrationconcentrated
  2. washwashed twice with 0.5% aqueous NaHCO3
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the crude product by column chromatography

Sources & evidence

ORD record
ord-4fc6b35319144df28c3a7ce2cc497b35
Source dataset
uspto-grants-1997_05
Patent number
US05633360

Reaction notes

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