Triethylsilane → HCID 22393547, compound

HRID 1454277Notes

Reaction equation

HRID 1454277 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:20])[N:7]3[CH:13]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:12][O:11][CH:8]32)=[CH:4][CH:3]=1.C([SiH](CC)CC)C.CCCCCC.C(OCC)(=O)C>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[OH:11][CH2:12][CH:13]([N:7]1[CH2:8][C:9]2[C:5](=[CH:4][CH:3]=[C:2]([CH3:1])[CH:10]=2)[C:6]1=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 12052TriethylsilaneHCID 20800573HCID 20800573, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 22393547HCID 22393547, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

8-methyl-3-phenyl-2,3-dihydro-9bH-oxazolo[2,3-a]isoindol-5-one (5.20 g, 19.60 mmol) was taken up in anhydrous DCM (100 mL) under argon and cooled to minus 78EC. Triethylsilane (9.12 g, 78.40 mmol, 12.52 mL) was added via syringe followed by titanium tetrachloride in DCM (1.0M, 58.80 mmol, 58.80 mL). The solution was stirred at minus 78EC for 5 h then allowed to warm to room temp and stir for 12 h. The reaction was slowly poured into ice and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with saturated sodium bicarbonate, water, brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (1:1 hexane/ethyl acetate) Yield 4.72 g. 1H NMR (CDCl3, 300 MHz): δ 2.40 (s, 3H), 4.12-4.42 (m, 5H), 5.31 (dd, J=4, 8 Hz, 1H), 7.10-7.39 (m, 7H), 7.67 (d, J=8, 1H).

Workup

  1. temperaturecooled to minus 78EC
  2. stirringstir for 12 h
  3. additionThe reaction was slowly poured into ice
  4. extractionthe aqueous layer was extracted three times with ethyl acetate
  5. washThe combined organic layers were washed with saturated sodium bicarbonate, water, brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe solution was filtered
  8. customthe solvent removed under reduced pressure
  9. customThe product was isolated by flash chromatography

Sources & evidence

ORD record
ord-4dd855b5015744c488b10841a564f621
Source dataset
uspto-grants-2009_01
Patent number
US07479495B2

Reaction notes

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