Tetrahydrofuran → HCID 53934341, compound

HRID 399070Notes

Reaction equation

HRID 399070 reaction equation
[Cl:1][C:2]1([Cl:21])[C:5](=O)[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:3]1[C:13]1[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=1.[CH2:22]1COCC1>[CH3-].C[Al]C.[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Cl-].[Ti+4]>[Cl:1][C:2]1([Cl:21])[C:3]([C:13]2[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=2)=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:5]1=[CH2:22]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 17881582HCID 17881582, compound

Product 1

HCID 53934341HCID 53934341, compound

Reagents, catalysts & solvents 1

HCID 91617563mu-Methylene-mu-chlorobis(eta5-2,4-cyclopentadien-1-yl)(dimethylaluminum)titaniumCatalyst

Procedure

To a solution of Example 1 (810 mg) in THF (20 mL) at 0° C. was added Tebbe's reagent (0.5M, 5 mL) dropwise. The mixture was stirred at r.t. for 30 min., quenched with NaOH 0.5N at 0° C. and diluted with Et2O. The organic phase was washed with H2O, brine, dried (MgSO4) and the solvents evaporated. Flash chromatography of the residue (silica gel; hexane/EtOAc (95:5)) provided the title compound as a yellow oil.

Workup

  1. customquenched with NaOH 0.5N at 0° C.
  2. additiondiluted with Et2O
  3. washThe organic phase was washed with H2O, brine
  4. dry with materialdried (MgSO4)
  5. customthe solvents evaporated

Sources & evidence

ORD record
ord-3b948e807a344f9c828fb43aaaeb0fc5
Source dataset
uspto-grants-1998_10
Patent number
US05817700

Reaction notes

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