2-Thienylmethyltriphenylphosphonium chloride → 2,2-Dimethylpropionic acid 2-{[3-benzyloxy-4-(2-thiophene-2-ylvinyl)-phenyl]methylamino}ethyl ester

HRID 85316Notes

Reaction equation

HRID 85316 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.[CH2:34]([O:41][C:42]1[CH:43]=[C:44]([CH2:50][NH:51][CH2:52][CH2:53][O:54][C:55](=[O:60])[C:56]([CH3:59])([CH3:58])[CH3:57])[CH:45]=[CH:46][C:47]=1[CH:48]=O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1COCC1>[CH2:34]([O:41][C:42]1[CH:43]=[C:44]([CH2:50][NH:51][CH2:52][CH2:53][O:54][C:55](=[O:60])[C:56]([CH3:59])([CH3:58])[CH3:57])[CH:45]=[CH:46][C:47]=1[CH:48]=[CH:7][C:3]1[S:2][CH:6]=[CH:5][CH:4]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 115747672-Thienylmethyltriphenylphosphonium chlorideHCID 86667598HCID 86667598, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 680086402,2-Dimethylpropionic acid 2-{[3-benzyloxy-4-(2-thiophene-2-ylvinyl)-phenyl]methylamino}ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Thiophene-2-ylmethyl triphenylphosphonium chloride (9.0 g, 22.7 mmol) was added to THF (80 ml), and PhLi (12.0 g of 19% solution in hexane, 27.2 mmol) was added dropwise thereto in an ice bath. After 20 minutes, 2,2-dimethylpropionic acid 2-[(3-benzyloxy-4-formylphenyl)methylamino]ethyl ester (7.0 g, 18.9 mmol) dissolved in THF (20 ml) was added dropwise. The mixture was reacted for 2 hours. After the reaction mixture was added to 300 ml of ice water, 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: 7.15 g (84.5%)).

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: 7.15 g (84.5%))

Sources & evidence

ORD record
ord-a7ec1d94742b436d8b9477cdd18be8a6
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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