Water → Dibutyl[3-methoxy-4-[2-(thiophene-2-yl)vinyl]phenyl]amine

HRID 85237Notes

Reaction equation

HRID 85237 reaction equation
C1([Li])C=CC=CC=1.[Cl-].[C:9]1([CH2:14][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:13][CH:12]=[CH:11][CH:10]=1.[CH2:34]([N:38]([CH2:49][CH2:50][CH2:51][CH3:52])[C:39]1[CH:46]=[CH:45][C:42]([CH:43]=O)=[C:41]([O:47][CH3:48])[CH:40]=1)[CH2:35][CH2:36][CH3:37].O>O1CCCC1.C(OCC)(=O)C>[CH2:34]([N:38]([CH2:49][CH2:50][CH2:51][CH3:52])[C:39]1[CH:46]=[CH:45][C:42]([CH:43]=[CH:14][C:9]2[S:13][CH:12]=[CH:11][CH:10]=2)=[C:41]([O:47][CH3:48])[CH:40]=1)[CH2:35][CH2:36][CH3:37]

Participants

7

Reactant 4

HCID 962WaterHCID 115747672-Thienylmethyltriphenylphosphonium chlorideHCID 146439034-(Dibutylamino)-2-methoxybenzaldehydeHCID 178506676HCID 178506676, compound

Product 1

HCID 68008836Dibutyl[3-methoxy-4-[2-(thiophene-2-yl)vinyl]phenyl]amineYield 89.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In a stream of argon, to 20 ml of tetrahydrofuran was added 2.4 g of phenyllithium (19% solution in dibutylether) (5.43 mmol), and 1.95 g (4.94 mmol) of 2-thenyl triphenylphosphonium chloride was added thereto under ice cooling. Next, 1.3 g (4.94 mmol) of 4-dibutylamino-2-methoxybenzaldehyde was dissolved in tetrahydrofuran and added dropwise. The mixture was stirred under ice cooling for 1.5 hours. After the reaction mixture was poured into water, extraction with ethyl acetate, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residue was purified by silica gel column chromatography to give 1.51 g of an orange oily matter (yield: 89.2%).

Workup

  1. additionwas added
  2. additionadded dropwise
  3. washwashing with a saturated saline solution
  4. dry with materialdrying over anhydrous sodium sulfate, and concentration
  5. customThe residue was purified by silica gel column chromatography
  6. customto give 1.51 g of an orange oily matter (yield: 89.2%)

Sources & evidence

ORD record
ord-1056e68868114c89a5930976d83b9ede
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

Loading…