Chlorotrimethylsilane → HCID 131719955, compound

HRID 52749Notes

Reaction equation

HRID 52749 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]2[CH2:5][CH2:6][C:3]=12.C(N(CC)CC)C.Cl[Si:18]([CH3:21])([CH3:20])[CH3:19]>C1C=CC=CC=1>[CH3:19][Si:18]([CH3:21])([CH3:20])[O:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]2[CH2:5][CH2:6][C:3]=12

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 214252094-Hydroxybenzocyclobutene

Product 1

HCID 131719955HCID 131719955, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
5 °C

Procedure

A larger batch of 4-trimethylsiloxybenzocyclobutene was synthesized from 6.56 gms of 4-hydroxybenzocyclobutene and 5.54 gms of triethylamine, taken up in 15 ml anhydrous benzene followed by the addition of a nearly three molar excess of chlorotrimethylsilane (20 ml in 15 ml dry benzene) to the reaction mixture maintained at 5° C. An instant white precipitation of triethylamine hydrochloride was observed. The solution was allowed to warm up on its own to 15° C. in about 5 hours and the reaction mixture was kept stirred overnight, It was warmed to 40° C. and maintained for about three hours. The reaction mixture was cooled and the isolation of the product was done exactly as described before. The weight of the light yellow oil (crude) was 7.93 g, 76% yield. Total amount of the colorless oil obtained from vacuum distillation was 7.07 grams. Anal. Calc.: C, 68.69%; H, 8.38%. Found: C, 69.15%; H, 8.44%.

Workup

  1. customAn instant white precipitation of triethylamine hydrochloride
  2. temperatureto warm up on its own to 15° C. in about 5 hours
  3. temperatureIt was warmed to 40° C.
  4. temperaturemaintained for about three hours
  5. temperatureThe reaction mixture was cooled
  6. customTotal amount of the colorless oil obtained from vacuum distillation

Sources & evidence

ORD record
ord-ca63de2d7e9a419c8f139687c0eb9182
Source dataset
uspto-grants-1997_04
Patent number
US05616765

Reaction notes

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