2-Thienylmethyltriphenylphosphonium chloride → HCID 68008944, compound

HRID 85310Notes

Reaction equation

HRID 85310 reaction equation
[Cl-].[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Li]C1C=CC=CC=1.[CH:34]([C:36]1[CH:41]=[CH:40][C:39]([CH2:42][NH:43][CH2:44][CH2:45][O:46][C:47](=[O:52])[C:48]([CH3:51])([CH3:50])[CH3:49])=[CH:38][C:37]=1[O:53][CH3:54])=O>C1COCC1>[CH3:54][O:53][C:37]1[CH:38]=[C:39]([CH2:42][NH:43][CH2:44][CH2:45][O:46][C:47](=[O:52])[C:48]([CH3:51])([CH3:50])[CH3:49])[CH:40]=[CH:41][C:36]=1[CH:34]=[CH:7][C:3]1[S:2][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 115747672-Thienylmethyltriphenylphosphonium chlorideHCID 866675952,2-Dimethylpropionic acid 2-[(4-formyl-3-methoxyphenyl)methylamino]ethyl esterHCID 178506676HCID 178506676, compound

Product 1

HCID 68008944HCID 68008944, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Thiophene-2-ylmethyl triphenylphosphonium chloride (4.4 g, 16.3 mmol) was added to THF (50 ml), and PhLi (8.6 g of 19% solution in hexane, 19.6 mmol) was added dropwise thereto in an ice bath. After 20 minutes, 2,2-dimethylpropionic acid 2-[(4-formyl-3-methoxyphenyl)methylamino]ethyl ester (4.0 g, 13.6 mmol) dissolved in THF (15 ml) was added dropwise. The mixture was reacted for 2 hours. The reaction mixture was added to 300 ml of ice water, and the oily matter was subjected to 3 times of extraction with dichloromethane (50 ml). Washing with a saturated saline solution, drying over Na2SO4, and concentration were performed. The residue was purified by silica gel chromatography to give a yellow oily matter (yield: 4.0 g (79.3%)).

Workup

  1. additionwas added dropwise
  2. additionwas added dropwise
  3. customThe mixture was reacted for 2 hours
  4. extractionthe oily matter was subjected to 3 times of extraction with dichloromethane (50 ml)
  5. washWashing with a saturated saline solution
  6. dry with materialdrying over Na2SO4, and concentration
  7. customThe residue was purified by silica gel chromatography
  8. customto give a yellow oily matter (yield: 4.0 g (79.3%))

Sources & evidence

ORD record
ord-7cb8099afe904d3d8770425afec16486
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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