Water → HCID 86667578, compound

HRID 85285Notes

Reaction equation

HRID 85285 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]([CH2:51][CH2:52][CH2:53][CH3:54])[C:39]1[CH:44]=[CH:43][C:42]([CH:45]=[CH:46][CH:47]=O)=[C:41]([O:49][CH3:50])[CH:40]=1)[CH2:35][CH2:36][CH3:37].O>O1CCCC1.C(OCC)(=O)C>[CH2:34]([N:38]([CH2:51][CH2:52][CH2:53][CH3:54])[C:39]1[CH:44]=[CH:43][C:42]([CH:45]=[CH:46][CH:47]=[CH:14][C:9]2[S:13][CH:12]=[CH:11][CH:10]=2)=[C:41]([O:49][CH3:50])[CH:40]=1)[CH2:35][CH2:36][CH3:37]

Participants

7

Reactant 4

HCID 962WaterHCID 115747672-Thienylmethyltriphenylphosphonium chlorideHCID 866675703-(4-Dibutylamino-2-methoxyphenyl)propenalHCID 178506676HCID 178506676, compound

Product 1

HCID 86667578HCID 86667578, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In a stream of argon, to 15 ml of tetrahydrofuran was added 1.68 g of phenyllithium (19% solution in dibutylether) (3.8 mmol), and 1.37 g (3.5 mmol) of 2-thenyl triphenylphosphonium chloride was added thereto under ice cooling. Next, 1.0 g (3.5 mmol) of 3-(4-dibutylamino-2-methoxyphenyl)propenal was dissolved in tetrahydrofuran and added dropwise. The mixture was stirred under ice cooling for 2 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 0.92 g of an orange oily matter (yield: 72.0%).

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 0.92 g of an orange oily matter (yield: 72.0%)

Sources & evidence

ORD record
ord-4d8927a64be74b8cbd9bfbd7da0cb672
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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