Water → Dibutyl[4-[2-[4-(tert-butyldiphenylsiloxymethyl)phenyl]vinyl]-3-methoxyphenyl]amine

HRID 85248Notes

Reaction equation

HRID 85248 reaction equation
C1([Li])C=CC=CC=1.[Br-].[O:9]([CH2:27][C:28]1[CH:53]=[CH:52][C:31]([CH2:32][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:30][CH:29]=1)[Si:10]([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:54]([N:58]([CH2:69][CH2:70][CH2:71][CH3:72])[C:59]1[CH:66]=[CH:65][C:62]([CH:63]=O)=[C:61]([O:67][CH3:68])[CH:60]=1)[CH2:55][CH2:56][CH3:57].O>O1CCCC1.C(OCC)(=O)C>[CH2:54]([N:58]([CH2:69][CH2:70][CH2:71][CH3:72])[C:59]1[CH:66]=[CH:65][C:62]([CH:63]=[CH:32][C:31]2[CH:30]=[CH:29][C:28]([CH2:27][O:9][Si:10]([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:53][CH:52]=2)=[C:61]([O:67][CH3:68])[CH:60]=1)[CH2:55][CH2:56][CH3:57]

Participants

7

Reactant 4

HCID 962WaterHCID 146439034-(Dibutylamino)-2-methoxybenzaldehydeHCID 88550422HCID 88550422, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 68008966Dibutyl[4-[2-[4-(tert-butyldiphenylsiloxymethyl)phenyl]vinyl]-3-methoxyphenyl]amineYield 94.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In a stream of argon, to 35 ml of tetrahydrofuran was added 3.33 g of phenyllithium (19% solution in dibutylether) (7.53 mmol), and 4.8 g (6.84 mmol) of 4-(tert-butyldiphenylsiloxymethyl)benzyltriphenylphosphonium bromide was added thereto under ice cooling. Next, 1.8 g (6.838 mmol) of 4-dibutylamino-2-methoxybenzaldehyde was dissolved in tetrahydrofuran and added dropwise. The mixture was stirred for 1.5 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. Ethyl acetate/hexane (5/1) was added to the residue and the precipitate was filtered off. The filtrate was reconcentrated and the residue was purified by silica gel column chromatography to give 3.92 g of a yellow liquid (yield: 94.7%).

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. additionEthyl acetate/hexane (5/1) was added to the residue
  6. filtrationthe precipitate was filtered off
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-60b245cf8d184c99ad5d0a9e6c1a6bff
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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