Water → Dibutyl[3-(tert-butyldiphenylsiloxy)-4-[2-(thiophene-2-yl)vinyl]phenyl]amine

HRID 85261Notes

Reaction equation

HRID 85261 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]([CH2:65][CH2:66][CH2:67][CH3:68])[C:39]1[CH:46]=[CH:45][C:42]([CH:43]=O)=[C:41]([O:47][Si:48]([C:61]([CH3:64])([CH3:63])[CH3:62])([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:40]=1)[CH2:35][CH2:36][CH3:37].O>O1CCCC1.C(OCC)(=O)C>[CH2:34]([N:38]([CH2:65][CH2:66][CH2:67][CH3:68])[C:39]1[CH:46]=[CH:45][C:42]([CH:43]=[CH:14][C:9]2[S:13][CH:12]=[CH:11][CH:10]=2)=[C:41]([O:47][Si:48]([C:61]([CH3:62])([CH3:64])[CH3:63])([C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:40]=1)[CH2:35][CH2:36][CH3:37]

Participants

7

Reactant 4

HCID 962WaterHCID 115747672-Thienylmethyltriphenylphosphonium chlorideHCID 866676032-(Tert-butyldiphenylsiloxy)-4-dibutylaminobenzaldehydeHCID 178506676HCID 178506676, compound

Product 1

HCID 68009142Dibutyl[3-(tert-butyldiphenylsiloxy)-4-[2-(thiophene-2-yl)vinyl]phenyl]amineYield 62.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In a stream of argon, to 30 ml of tetrahydrofuran was added 3.17 g of phenyllithium (19% solution in dibutylether) (7.16 mmol), and 2.57 g (6.5 mmol) of 2-thenyl triphenylphosphonium chloride was added thereto under ice cooling. Next, 3.17 g (6.5 mmol) of 4-dibutylamino-2-tert-butyldiphenylsiloxybenzaldehyde was dissolved in tetrahydrofuran and added dropwise. The mixture was stirred for 3 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 2.32 g of a yellowish brown oily matter (yield: 62.9%).

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 2.32 g of a yellowish brown oily matter (yield: 62.9%)

Sources & evidence

ORD record
ord-486c23fe233c4e879c85da90a3ba00a0
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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