Water → [3-Benzyloxy-4-(2-thiophene-2-ylvinyl)phenyl]butyl [4-(tert-butyldiphenylsiloxy)butyl]amine

HRID 85331Notes

Reaction equation

HRID 85331 reaction equation
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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.C(OC1C=C([N:50]([CH2:73][CH2:74][CH2:75][CH3:76])[CH2:51][CH2:52][CH2:53][CH2:54][O:55][Si:56]([C:69]([CH3:72])([CH3:71])[CH3:70])([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)C=CC=1C=O)C1C=CC=CC=1.O.[C:78]([O:81][CH2:82][CH3:83])(=O)C>O1CCCC1>[CH2:78]([O:81][C:82]1[CH:83]=[C:3]([CH2:76][CH2:75][CH2:74][CH2:73][NH:50][CH2:51][CH2:52][CH2:53][CH2:54][O:55][Si:56]([C:69]([CH3:72])([CH3:71])[CH3:70])([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C:63]2[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=2)[CH:2]=[CH:1][C:6]=1[CH:5]=[CH:14][C:9]1[S:13][CH:12]=[CH:11][CH:10]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 962WaterHCID 8857Ethyl AcetateHCID 115747672-Thienylmethyltriphenylphosphonium chlorideHCID 86667608HCID 86667608, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 68009024[3-Benzyloxy-4-(2-thiophene-2-ylvinyl)phenyl]butyl [4-(tert-butyldiphenylsiloxy)butyl]amineYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a stream of argon, to 20 ml of tetrahydrofuran was added 1.7 g of phenyllithium (19% solution in dibutylether) (3.83 mmol), and 1.38 g (3.49 mmol) of 2-thenyl triphenylphosphonium chloride was added thereto under ice cooling over 5 minutes. After the mixture was stirred for 10 minutes, 2.07 g (3.49 mmol) of 2-benzyloxy-4-[butyl[4-(tert-butyldiphenylsiloxy)butyl]amino]benzaldehyde dissolved in 50 ml of tetrahydrofuran was added dropwise thereto over 8 minutes. 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 2.03 g of a light brown oily matter (yield: 86.4%).

Workup

  1. additionwas added
  2. additionwas added dropwise
  3. waitover 8 minutes
  4. stirringThe mixture was stirred under ice cooling for 2 hours
  5. washwashing with a saturated saline solution
  6. dry with materialdrying over anhydrous sodium sulfate, and concentration
  7. customThe residue was purified by silica gel column chromatography
  8. customto give 2.03 g of a light brown oily matter (yield: 86.4%)

Sources & evidence

ORD record
ord-97491e9a35f049f588c53c75dd79c127
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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