Triethylsilane → HCID 71008327, compound

HRID 2361721Notes

Reaction equation

HRID 2361721 reaction equation
[SiH](CC)(CC)CC.O=[C:9]1[CH:17]2[CH2:18][C:13]3([NH:20][C:21](=[O:23])[CH3:22])[CH2:14][CH:15]([CH2:19][CH:11]([CH2:12]3)[O:10]1)[CH2:16]2>C(Cl)(Cl)Cl.O>[C:13]12([NH:20][C:21](=[O:23])[CH3:22])[CH2:18][CH:17]3[CH2:16][CH:15]([CH2:19][CH:11]([O:10][CH2:9]3)[CH2:12]1)[CH2:14]2

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 12012915HCID 12012915, compound

Product 1

HCID 71008327HCID 71008327, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

InBr3 (0.056 mmol) and Et3SiH (12.6 mmol) were successively added to a solution of lactone 16A (0.54 mmol) in CHCl3 (5 mL) and the reaction mixture was heated at 60° C. for 1 h. The reaction mixture was allowed to cool to rt, was diluted with H2O (10 mL), and the layers were separated. The aqueous layer was extracted with DCM (3×10 mL) and the combined organic layers were dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography (10/90 to 30/70 EtOAc/hexane) to provide ether 16B in 70% yield. Data: LC/MS (ESR) m/z 210 [M+1]+.

Workup

  1. temperatureto cool to rt
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with DCM (3×10 mL)
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (10/90 to 30/70 EtOAc/hexane)

Sources & evidence

ORD record
ord-2368dd72367a4b329e22a53a9aab0d35
Source dataset
uspto-grants-2014_04
Patent number
US08691808B2

Reaction notes

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