Triethylsilane → HCID 89872740, compound

HRID 515396Notes

Reaction equation

HRID 515396 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[CH2:9][CH2:10][C:11](=[O:14])[CH2:12]O)=[CH:4][CH:3]=1.C([SiH](CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[O:15][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 89872760HCID 89872760, compound

Product 1

HCID 89872740HCID 89872740, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask containing 1-(4-bromophenyl)-5-hydroxypentane-1,4-dione (800 mg, 2.95 mmol) was added DCM (40 ml). The solution was cooled under an ice-bath and a solution of Boron trifluroide (diethyl ether complex, 0.89 ml, 7.00 mmol) was added dropwise. After the addition, triethylsilane (1.11 ml, 6.96 mmol) was also added and the reaction was stirred in an ice-bath for 85 minutes. The mixture was quenched with a saturated of NaHCO3 and was extracted twice with DCM. The combined organic portions was dried over sodium sulfate, filtered and concentrated to afford a crude residue. Column purification afforded the title compound as thick oil (638 mg, 84% conversion). MS (ESI) m/z, non-ionizable. Retention time 1.17 min. (Condition X).

Workup

  1. temperatureThe solution was cooled under an ice-bath
  2. additiona solution of Boron trifluroide (diethyl ether complex, 0.89 ml, 7.00 mmol) was added dropwise
  3. additionwas also added
  4. customThe mixture was quenched with a saturated of NaHCO3
  5. extractionwas extracted twice with DCM
  6. dry with materialThe combined organic portions was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a crude residue
  10. customColumn purification

Sources & evidence

ORD record
ord-31c3467d5eab4d8ebbc57f0f835101d9
Source dataset
uspto-grants-2015_08
Patent number
US09108956B2

Reaction notes

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