Chloroform → HCID 67381626, compound

HRID 1805740Notes

Reaction equation

HRID 1805740 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[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:31](Cl)([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([C:40]1[CH:47]=[CH:46][C:43]([O:44][CH3:45])=[CH:42][CH:41]=1)[C:32]1[CH:39]=[CH:38][C:35]([O:36][CH3:37])=[CH:34][CH:33]=1.C(Cl)(Cl)Cl>CO>[OH:8][CH2:9][C:10]1[CH:11]=[C:12]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:13]=[C:14]([CH2:16][O:17][C:31]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)([C:40]2[CH:47]=[CH:46][C:43]([O:44][CH3:45])=[CH:42][CH:41]=2)[C:32]2[CH:39]=[CH:38][C:35]([O:36][CH3:37])=[CH:34][CH:33]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 67381688HCID 67381688, compound

Product 1

HCID 67381626HCID 67381626, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10.7 ml of pyrizine was added to dissolve 0.4596 g of Compound (2) in an Ar atmosphere, and 0.9547 g (2.80 mmol, 1.3 eq) of DMTrCl was added. This was agitated for 96 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 0.4231 g (0.82 mmol, 38%) of Compound (3) was isolated by silica gel chromatography (chloroform:methanol=100:1).

Workup

  1. addition10.7 ml of pyrizine was added
  2. additionwas added
  3. extractionAfter extraction with chloroform the organic layer
  4. washwas 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-3bc3b394b12945198f072424b06ac9ee
Source dataset
uspto-grants-2013_01
Patent number
US08354515B2

Reaction notes

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