Chloroform → 2-[2-(4-Dibutylamino-2,6-dimethoxyphenyl)vinyl]thiophene

HRID 85305Notes

Reaction equation

HRID 85305 reaction equation
C1([Li])C=CC=CC=1.[Br-].[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH2:14][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:34]([N:38]([CH2:51][CH2:52][CH2:53][CH3:54])[C:39]1[CH:46]=[C:45]([O:47][CH3:48])[C:42]([CH:43]=O)=[C:41]([O:49][CH3:50])[CH:40]=1)[CH2:35][CH2:36][CH3:37].C(Cl)(Cl)Cl>O1CCCC1>[CH2:34]([N:38]([CH2:51][CH2:52][CH2:53][CH3:54])[C:39]1[CH:46]=[C:45]([O:47][CH3:48])[C:42]([CH:43]=[CH:14][C:10]2[S:9][CH:13]=[CH:12][CH:11]=2)=[C:41]([O:49][CH3:50])[CH:40]=1)[CH2:35][CH2:36][CH3:37]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 10741697Triphenyl(2-thienylmethyl)phosphonium BromideHCID 86667593HCID 86667593, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 680091252-[2-(4-Dibutylamino-2,6-dimethoxyphenyl)vinyl]thiopheneYield 62.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a stream of argon, to 30 ml of tetrahydrofuran was added 3.76 g of a 19% phenyllithium solution (8.5 mmol), and 0.78 g (1.98 mmol) of thiophene-2-ylmethyltriphenylphosphonium bromide was added thereto under cooling. After the mixture was well-stirred, 0.58 g (1.98 mmol) of 4-dibutylamino-2,6-dimethoxybenzaldehyde dissolved in 3 ml of tetrahydrofuran was added dropwise. The mixture was stirred for 1.5 hours. After the mixture was poured into 70 ml of ice water, extraction with 200 ml of chloroform, washing with a saturated saline solution, drying over anhydrous magnesium sulfate, and concentration were performed. The residue was purified by silica gel chromatography to give 463 mg (yield: 62%) of 2-[2-(4-dibutylamino-2,6-dimethoxyphenyl)vinyl]thiophene as a dark purple crystal (mp: 90° C.)

Workup

  1. additionwas added
  2. temperatureunder cooling
  3. additionwas added dropwise
  4. stirringThe mixture was stirred for 1.5 hours
  5. washwashing with a saturated saline solution
  6. dry with materialdrying over anhydrous magnesium sulfate, and concentration
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1f3c1e039c164e3992e011ecc59e3f74
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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