Triethoxysilane → Benzoxazole

HRID 1618059Notes

Reaction equation

HRID 1618059 reaction equation
C(O[SiH](OCC)OCC)C.C(OC1C=CC([C:21]2[O:22][C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=3[N:25]=2)=CC=1)C=C>C1(C)C=CC=CC=1>[O:22]1[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=[CH:21]1

Participants

4

Reactant 2

HCID 13830Triethoxysilane2×HCID 135703742-{4-[(Prop-2-en-1-yl)oxy]phenyl}-1,3-benzoxazole

Product 1

HCID 9228Benzoxazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A 250 ml round bottom flask, equipped with a reflux condenser and an oil bath with a magnetic stirrer was charged with 4.0 g (22 mmol) triethoxysilane and 5.0 g (20 mmol) of the above 2-(4-allyloxyphenyl)-benzoxazole in 100 ml of toluene under nitrogen atmosphere. The reaction mixture was heated to 70° C. and a catalytic amount of divinyl-tetramethyl disiloxane platinum complex was added. After the reaction mixture was heated for 2 hours, another 1.8 g (11 mmol) triethoxysilane were added and the reaction mixture was stirred over night. The product solution was evaporated, diluted with toluene and filtrated over Celite to yield 8 g (96%) of crude (4-(3-(triethoxysilyl)propyloxy])phenyl)-benzoxazole. UV (ethanol) 308 nm (23′468).

Workup

  1. customA 250 ml round bottom flask, equipped with a reflux condenser and an oil bath with a magnetic stirrer
  2. additiona catalytic amount of divinyl-tetramethyl disiloxane platinum complex was added
  3. temperatureAfter the reaction mixture was heated for 2 hours
  4. customThe product solution was evaporated
  5. additiondiluted with toluene
  6. filtrationfiltrated over Celite

Sources & evidence

ORD record
ord-203094d34b1b423490aa42a826ce92ba
Source dataset
uspto-grants-2014_07
Patent number
US08765967B2

Reaction notes

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