Hexane → HCID 13124064, compound

HRID 583588Notes

Reaction equation

HRID 583588 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C([S:10][C:11]1[CH:16]=[CH:15][CH:14]=CC=1)C=C.[CH2:17]([Al](CC)CC)C>O>[C:3]1([S:10][CH2:11][CH:16]([CH3:17])[CH2:15][CH3:14])[CH:2]=[CH:1][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 79180(Allylthio)benzeneHCID 16682930Triethylaluminum

Product 1

HCID 13124064HCID 13124064, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Hexane (1 ml) was added to (cyclopentadienyl)(1-[(1'S,2'S,5'R)-2'-isopropyl-5'-methylcyclohexyl]-4,5,6,7-tetrahydroindenyl)zirconium dichloride complex (20 mg, 4 mol %, prepared as in Example 1) in a 25 ml schlenk flask containing a stirring bar. Allylphenylthioether (150 mg, 1 mmol) was added and the flask evacuated and refilled 3 times with argon. Triethylaluminum (6 ml, 1.0 M in hexane, 6 mmol, 6 eq) was added dropwise. The solution turned yellow and was left for 72 hours. Water (10 ml) was added dropwise, the organics were extracted with diethylether (3×5 ml) and the combined extracts were dried over magnesium sulphate. The solvents were removed under reduced pressure and Kugelrohr distillation yielded the title compound as a clear liquid (145 mg, 0.85 mmnol, 80.5% yield, e.e 57% (FS-Hydrodex-B, 110° C.)).

Workup

  1. additioncontaining a stirring bar
  2. customthe flask evacuated
  3. additionrefilled 3 times with argon
  4. extractionthe organics were extracted with diethylether (3×5 ml)
  5. dry with materialthe combined extracts were dried over magnesium sulphate
  6. customThe solvents were removed under reduced pressure and Kugelrohr distillation

Sources & evidence

ORD record
ord-b6547e5b490a4b918955451e374db46a
Source dataset
uspto-grants-1999_07
Patent number
US05929266

Reaction notes

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