Triethylsilane → HCID 67245862, compound

HRID 2425318Notes

Reaction equation

HRID 2425318 reaction equation
[SiH](CC)(CC)CC.[CH2:8]([O:10][C:11](=[O:40])[C:12]([NH:36][C:37](=[O:39])[CH3:38])([CH:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:24]=2)[C:19]1=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH3:9]>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH2:8]([O:10][C:11](=[O:40])[C:12]([NH:36][C:37](=[O:39])[CH3:38])([CH:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:24]=2)[CH2:19]1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH3:9]

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 67246761HCID 67246761, compound

Product 1

HCID 67245862HCID 67245862, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Et3SiH (1.014 g, 8.704 mmol) in CH2Cl2 (8 mL) was added 4 (0.213 g, 0.465 mmol) in CH2Cl2 (1.5 mL) dropwise at room temp under N2. TiCl4 (0.354 g, 1.858 mmol) was then added and the reaction left to stir at room temp over night. The reaction was then poured slowly over ice and extracted with CH2Cl2, the organic layer was then dried and concentrated. The product was then purified with silica gel chromatography eluding with 70% hexanes-30% EtOAc. The reaction provided 5 (0.149 g, 0.336 mmol, 72%).

Workup

  1. waitthe reaction left
  2. additionThe reaction was then poured slowly over ice
  3. extractionextracted with CH2Cl2
  4. customthe organic layer was then dried
  5. concentrationconcentrated
  6. customThe product was then purified with silica gel chromatography

Sources & evidence

ORD record
ord-d559a71e1a9f4c9a856f4445a8a9955d
Source dataset
uspto-grants-2011_06
Patent number
US07964649B2

Reaction notes

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