Tetrahydrofuran → HCID 68008741, compound

HRID 85343Notes

Reaction equation

HRID 85343 reaction equation
O1CCCC1.C1([Li])C=CC=CC=1.[Br-].[OH:14][CH2:15][C:16]1[CH:41]=[CH:40][C:19]([CH2:20][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:18][CH:17]=1.[CH2:42]([N:46]([CH2:55][CH2:56][CH2:57][CH3:58])[C:47]1[CH:54]=[CH:53][C:50]([CH:51]=O)=[CH:49][CH:48]=1)[CH2:43][CH2:44][CH3:45]>C1(C)C=CC=CC=1.O>[CH2:42]([N:46]([CH2:55][CH2:56][CH2:57][CH3:58])[C:47]1[CH:48]=[CH:49][C:50]([CH:51]=[CH:20][C:19]2[CH:18]=[CH:17][C:16]([CH2:15][OH:14])=[CH:41][CH:40]=2)=[CH:53][CH:54]=1)[CH2:43][CH2:44][CH3:45]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 6053914-(Dibutylamino)benzaldehydeHCID 86667618HCID 86667618, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 68008741HCID 68008741, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

In a stream of argon, to 40 ml of tetrahydrofuran was added 8.0 g of phenyllithium (19% solution in dibutylether) (18.1 mmol). To this mixture, 3.81 g (8.2 mmol) of 4-(hydroxymethyl)benzyltriphenylphosphonium bromide was added under cooling. After the mixture was stirred at the same temperature, 2.0 g (8.6 mmol) of 4-(dibutylamino)benzaldehyde was added thereto. The mixture was stirred at the same temperature for 1 hour. After the reaction mixture was added to water, extraction with toluene, washing with a saturated saline solution, and drying over anhydrous sodium sulfate were performed. Toluene was evaporated off. The residue was purified by silica gel column chromatography to give 2.37 g of a yellow liquid (yield: 85.5%).

Workup

  1. temperatureunder cooling
  2. additionwas added
  3. washwashing with a saturated saline solution
  4. dry with materialdrying over anhydrous sodium sulfate
  5. customToluene was evaporated off
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-77a53e34a9f4414cbf10940baf7812ea
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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