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Chemical Structure| 87184-81-4 Chemical Structure| 87184-81-4

Structure of 87184-81-4

Chemical Structure| 87184-81-4

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Product Details of [ 87184-81-4 ]

CAS No. :87184-81-4
Formula : C10H22O2Si
M.W : 202.37
SMILES Code : O=CCCCO[Si](C)(C(C)(C)C)C
MDL No. :MFCD12025097
InChI Key :DOHGFFVYNCRCEV-UHFFFAOYSA-N
Pubchem ID :10888976

Safety of [ 87184-81-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 87184-81-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 87184-81-4 ]

[ 87184-81-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 4102-60-7 ]
  • [ 87184-81-4 ]
  • (13Z,16Z)-1-((tert-butyldimethylsilyl)oxy)docosa-13,16-dien-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
4.91 g Preparation of Intermediate A2: (13Z, 16Z)-1 -((tert- butyldimethylsilyl)oxy)docosa-13, 16-dien-4-ol. [0375] In a 500 ml_ three neck round-bottom flask equipped with a stir bar Mg turnings (0.443 g, 18.22 mmol) was weighed out, and held under vacuum for 5 minutes while being heated with a heat gun. The flask was left under vacuum for 5-10 minutes. The flask was then filled with N2, and sealed with a septa. THF (75 ml_) was poured quickly into the reaction vessel, followed by l2 (0.039 g, 0.152 mmol) and Intermediate A1 (5 g, 15.18 mmol), and a reflux condenser was fitted to the flask. The whole system was exchanged with N2 three times, and the mixture was heated to reflux (90C) for 2 hours. The clear mixture was then cooled to room temperature under N2. [0376] In a second 250 ml_ round-bottom flask, 4-((tert-butyldimethylsilyl)oxy)butanal (2.76 g, 13.66 mmol) was dissolved in THF (30 ml_) and cooled in an ice-water bath. The prepared linoleyl Grignard reagent was then added to the aldehyde dropwise over 10 minutes by syringe, and the reaction stirred at ambient temperature for 30 minutes. The reaction flask was cooled again in an ice-bath, saturated NH4CI (aq.) solution was added slowly to adjust pH to 7, and reaction stirred, warming to room temperature over 1 hour. Brine and ethyl acetate were added to the mixture in a separatory funnel. The organics were collected and washed with brine, dried over MgS04, filtered and concentrated under reduced pressure to give crude product mixture. The crude was then purified by silica gel column chromatography eluting with 0-20% ethyl acetate in heptane to afford 4.91 g product as a colorless oil. 1H NMR (400 MHz, CDCI3) delta = 5.26 - 5.46 (m, 4 H) 3.51 - 3.80 (m, 3 H) 2.71 - 2.84 (m, 2 H) 1 .99 - 2.13 (m, 4 H) 1 .56 - 1 .75 (m, 4 H) 1 .21 - 1 .52 (m, 20 H) 0.82 - 0.98 (m, 12 H) 0.01 - 0.14 (m, 6 H) ppm.
 

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