Triethoxysilane → 2-methoxy-4-[(E)2-methoxycarbonyl-vinyl]phenyl 4-(4-triethoxysilanylbutyloxy)benzoate

HRID 1739493Notes

Reaction equation

HRID 1739493 reaction equation
[CH2:1]([O:5][C:6]1[CH:28]=[CH:27][C:9]([C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])=[CH:15][C:14]=2[O:25][CH3:26])=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH:3]=[CH2:4].[CH2:29]([O:31][SiH:32]([O:36][CH2:37][CH3:38])[O:33][CH2:34][CH3:35])[CH3:30]>C([Si](C=C)(C)O[Si](C)(C)C)=C.[Pt].C1(C)C=CC=CC=1>[CH2:29]([O:31][Si:32]([O:36][CH2:37][CH3:38])([O:33][CH2:34][CH3:35])[CH2:4][CH2:3][CH2:2][CH2:1][O:5][C:6]1[CH:28]=[CH:27][C:9]([C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])=[CH:15][C:14]=2[O:25][CH3:26])=[O:11])=[CH:8][CH:7]=1)[CH3:30]

Participants

5

Reactant 2

HCID 13830Triethoxysilane2×HCID 21841372HCID 21841372, compound

Product 1

HCID 218412092-methoxy-4-[(E)2-methoxycarbonyl-vinyl]phenyl 4-(4-triethoxysilanylbutyloxy)benzoate

Reagents, catalysts & solvents 2

HCID 86614225Platinum divinyltetramethyldisiloxaneCatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Air was conducted for 30 min. into a mixture of 1 g of 2-methoxy-4-[(E)2-methoxycarbonyl-vinyl]phenyl 4-(3-butenyloxy)benzoate, 0.480 ml of triethoxysilane, 10 ml of toluene and 0.017 ml of platinum divinyltetramethyldisiloxane (3-3.5% in toluene) and the mixture was then stirred at 60° C. for 1 hr. Then, a further 0.1 ml of triethoxysilane was added and the mixture was left to react at 60° C. for 16 hrs. The reaction mixture was thereafter cooled to room temperature and partitioned between ethyl acetate and water. The organic phase was thereupon dried over magnesium sulphate, filtered and evaporated to dryness. Chromatography on 150 g of silica gel with toluene/ethyl acetate (19:1 to 9:1) gave 0.60 g of 2-methoxy-4-[(E)2-methoxycarbonyl-vinyl]phenyl 4-(4-triethoxysilanylbutyloxy)benzoate as a colorless liquid, λmax. (CH2Cl2): 279 nm.

Workup

  1. waitthe mixture was left
  2. customto react at 60° C. for 16 hrs
  3. temperatureThe reaction mixture was thereafter cooled to room temperature
  4. custompartitioned between ethyl acetate and water
  5. dry with materialThe organic phase was thereupon dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-d2945cece13f4c8ba2f92c02530eb2f9
Source dataset
uspto-grants-1999_10
Patent number
US05965761

Reaction notes

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