Water → Dibutyl[4-[2-[4-(tert-butyldiphenylsiloxymethyl)-2,5-dimethylphenyl]vinyl]-3-methoxyphenyl]amine

HRID 85254Notes

Reaction equation

HRID 85254 reaction equation
C1([Li])C=CC=CC=1.[Br-].[O:9]([CH2:27][C:28]1[C:53]([CH3:54])=[CH:52][C:31]([CH2:32][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[C:30]([CH3:55])[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.[CH2:56]([N:60]([CH2:71][CH2:72][CH2:73][CH3:74])[C:61]1[CH:68]=[CH:67][C:64]([CH:65]=O)=[C:63]([O:69][CH3:70])[CH:62]=1)[CH2:57][CH2:58][CH3:59].O>O1CCCC1.C(OCC)(=O)C>[CH2:56]([N:60]([CH2:71][CH2:72][CH2:73][CH3:74])[C:61]1[CH:68]=[CH:67][C:64]([CH:65]=[CH:32][C:31]2[CH:52]=[C:53]([CH3:54])[C:28]([CH2:27][O:9][Si:10]([C:23]([CH3:25])([CH3:24])[CH3:26])([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:29][C:30]=2[CH3:55])=[C:63]([O:69][CH3:70])[CH:62]=1)[CH2:57][CH2:58][CH3:59]

Participants

7

Reactant 4

HCID 962WaterHCID 146439034-(Dibutylamino)-2-methoxybenzaldehydeHCID 885504254-(Tert-butyldiphenylsiloxymethyl)-2,5-dimethylbenzyltriphenylphosphonium bromideHCID 178506676HCID 178506676, compound

Product 1

HCID 68008984Dibutyl[4-[2-[4-(tert-butyldiphenylsiloxymethyl)-2,5-dimethylphenyl]vinyl]-3-methoxyphenyl]amineYield 89.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In a stream of argon, to 20 ml of tetrahydrofuran was added 2.54 g of phenyllithium (19% solution in dibutylether) (5.74 mmol), and 3.57 g (4.89 mmol) of 4-(tert-butyldiphenylsiloxymethyl)-2,5-dimethylbenzyltriphenylphosphonium bromide was added thereto under ice cooling. Next, 1.26 g (4.78 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. The residue was purified by silica gel column chromatography to give 2.7 g of an orange liquid (yield: 89.1%).

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

Sources & evidence

ORD record
ord-015dbccd06094c5ea30f97f734f19503
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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