Chlorotrimethylsilane → HCID 57425829, compound

HRID 1727305Notes

Reaction equation

HRID 1727305 reaction equation
[Li]CCCC.C(NC(C)C)(C)C.[CH2:13]([O:20][CH2:21][CH:22]1[CH2:25][C:24](=[O:26])[CH2:23]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)=O.CC(C)=O.[CH3:34][Si:35](Cl)([CH3:37])[CH3:36]>C1COCC1>[CH2:13]([O:20][CH2:21][CH:22]1[CH2:25][C:24]([O:26][Si:35]([CH3:37])([CH3:36])[CH3:34])=[CH:23]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 118198503-((Benzyloxy)methyl)cyclobutanoneHCID 18522661Acetone cardiceHCID 178418339Butyllithium

Product 1

HCID 57425829HCID 57425829, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-5 °C

Procedure

In a 1 L flask charged with argon, dry THF 300 ml was added. This was cooled to −5° C., then n-BuLi (83 ml, 1.6M in hexane, 0.132 mol) was added. After mixing 5 min, diisopropylamine (18 ml, 0.132 mol) was added drop by drop. After stirring for 10 min, this solution was cooled to −78° C. Then a THF solution of 3-(benzyloxymethyl)-cyclobutanone (20 g, 0.11 mol) was added drop by drop at −78° C. After addition, replace the dry ice-acetone bath with ice-water bath. After stirring at 0° C. for 30 min, TMSCl (16 ml, 0.132 mol) was added dropwise, this was stirred at 0° C. for 1 hr and room temperature for 10 min. Then the solvents were removed and the residue was washed with dry pentane and filtered. The filtrate was concentrated to give crude product without further purification. 1H NMR (CDCl3, 600 MHz): δ 0.23 (s, 9H), 2.20 (dd, J=12.6, 1.2, 1H), 2.65 (m, 1H), 2.74 (dd, J=13.2, 4.2, 1H), 3.41 (m, 1H), 3.48 (m, 1H), 4.54 (s, 2H), 4.67 (s, 1H), 7.26-7.35 (m, 5H). 13C NMR (CDCl3, 150 MHz): δ 0.09, 32.70, 38.18, 73.26, 75.41, 93.69, 104.27, 127.70, 127.86, 128.55, 138.20.

Workup

  1. additionwas added
  2. additionAfter mixing 5 min
  3. temperaturethis solution was cooled to −78° C
  4. additionAfter addition
  5. stirringAfter stirring at 0° C. for 30 min
  6. stirringthis was stirred at 0° C. for 1 hr and room temperature for 10 min
  7. customThen the solvents were removed
  8. washthe residue was washed with dry pentane
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated
  11. customto give crude product
  12. customwithout further purification

Sources & evidence

ORD record
ord-827eeeb2de1546999346af8045856feb
Source dataset
uspto-grants-2009_02
Patent number
US07495006B2

Reaction notes

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