1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 15546053, compound

HRID 244258Notes

Reaction equation

HRID 244258 reaction equation
[CH2:1]1[C@@:6]2([CH2:9][OH:10])[C@@H:7]([OH:8])[C@H:3]([C@H:4]([N:11]3[CH:18]=[CH:17][C:15](=[O:16])[NH:14][C:12]3=[O:13])[O:5]2)[O:2]1.[CH3:19][O:20][C:21]1[CH:42]=[CH:41][C:24]([C:25](Cl)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)=[CH:23][CH:22]=1.C(=O)(O)[O-].[Na+]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH3:33][O:32][C:29]1[CH:28]=[CH:27][C:26]([C:25]([O:10][CH2:9][C@@:6]23[CH2:1][O:2][C@@H:3]([C@H:4]([N:11]4[CH:18]=[CH:17][C:15](=[O:16])[NH:14][C:12]4=[O:13])[O:5]2)[C@@H:7]3[OH:8])([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:24]2[CH:41]=[CH:42][C:21]([O:20][CH3:19])=[CH:22][CH:23]=2)=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 516892Sodium BicarbonateHCID 15546052HCID 15546052, compound

Product 1

HCID 15546053HCID 15546053, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent2×

Procedure

To Compound 7 (140 mg, 0.53 mmol), anhydrous pyridine was added, followed by performing azeotropy of the mixture 3 times. Then, the product was converted into an anhydrous pyridine solution (1.5 ml), and 4,4′-dimethoxytrityl chloride (210 mg, 0.63 mmol) and DMAP (6.5 mg, 0.053 mmol) were added at room temperature in a stream of nitrogen. The mixture was stirred for 5 hours at room temperature. To the reaction mixture, a saturated sodium bicarbonate solution was added, followed by extraction with CH2Cl2. The organic phase was washed with water and a saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. After the solvents were distilled off under reduced pressure, the resulting crude product was purified by silica gel column chromatography (CHCl3:MeOH=40:1) to obtain Compound 8 (230 mg, 0.34 mmol, 66%).

Workup

  1. additionwere added at room temperature in a stream of nitrogen
  2. extractionfollowed by extraction with CH2Cl2
  3. washThe organic phase was washed with water
  4. dry with materiala saturated sodium chloride solution, and then dried over anhydrous sodium sulfate
  5. distillationAfter the solvents were distilled off under reduced pressure
  6. customthe resulting crude product was purified by silica gel column chromatography (CHCl3:MeOH=40:1)

Sources & evidence

ORD record
ord-6411048d47b440de883baf86cecdaa86
Source dataset
uspto-grants-2014_02
Patent number
USRE044779E1

Reaction notes

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