Triethoxy(3-isocyanatopropyl)silane → HCID 21841380, compound

HRID 1739497Notes

Reaction equation

HRID 1739497 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14](/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])[CH:13]=[CH:12]2.[CH2:25]([O:27][Si:28]([O:38][CH2:39][CH3:40])([O:35][CH2:36][CH3:37])[CH2:29][CH2:30][CH2:31][N:32]=[C:33]=[O:34])[CH3:26].C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC>C(Cl)Cl>[CH2:36]([O:35][Si:28]([O:38][CH2:39][CH3:40])([O:27][CH2:25][CH3:26])[CH2:29][CH2:30][CH2:31][NH:32][C:33]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14](/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])[CH:13]=[CH:12]2)=[O:34])[CH3:37]

Participants

5

Reactant 3

HCID 90613Triethoxy(3-isocyanatopropyl)silaneHCID 9809426Di-n-butyldilauryltin2×HCID 21841221HCID 21841221, compound

Product 1

HCID 21841380HCID 21841380, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 500 mg of methyl (E)-3-[6-(6-hydroxyhexyloxy)naphthalen-2-yl]acrylate, 25 ml of methylene chloride, 0.376 ml of 3-triethoxysilanylpropyl isocyanate and 0.009 ml of dibutyltin dilaurate was heated under reflux for 3 hrs. Thereafter, a further 0.009 ml of dibutyltin dilaurate was added and the mixture was left to react under reflux for 16 hrs. Then, the reaction solution was cooled to room temperature, evaporated completely and the residue was chromatographed on 150 g of silica gel with ether/hexane. This gave 830 mg of methyl 3-{6-[6-(3-triethoxysilanylpropylcarbamoyloxy)hexyloxy]naphthalen-2-yl}acrylate as a colorless solid, λmax. (CH2Cl2): 326 nm (ε=26200).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hrs
  3. waitthe mixture was left
  4. customto react
  5. temperatureunder reflux for 16 hrs
  6. customevaporated completely
  7. customthe residue was chromatographed on 150 g of silica gel with ether/hexane

Sources & evidence

ORD record
ord-a9b2723a4f714c5997f269842c4b2e8a
Source dataset
uspto-grants-1999_10
Patent number
US05965761

Reaction notes

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