Toluene → HCID 57910788, compound

HRID 1968659Notes

Reaction equation

HRID 1968659 reaction equation
[CH3:1][C:2]([C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=O)=[CH:22][CH:21]=1)([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:8][N:7]=1)[CH:3]([CH3:5])[CH3:4].[C:30]1(C)C=CC=CC=1>C1COCC1.[CH3-].C[Al+]C.[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Cl-].[Ti+3]>[CH3:27][O:26][C:24]([C:23]1[CH:28]=[CH:29][C:20]([C:2]([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[CH:8][N:7]=2)([CH3:1])[CH:3]([CH3:5])[CH3:4])=[CH:21][CH:22]=1)=[CH2:30]

Participants

5

Reactant 2

HCID 1140TolueneHCID 57910813HCID 57910813, compound

Product 1

HCID 57910788HCID 57910788, compound

Reagents, catalysts & solvents 2

HCID 53384502mu-Chlorobis(eta5-cyclopentadienyl)(dimethylaluminum)-mu-methylenetitaniumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Tebbe reagent (15.2 mL of a 0.5 M solution in toluene, 7.60 mmol) was added to a stirred solution of 1a (2.70 g, 6.91 mmol) in THF (100 mL) at rt and the resulting mixture aged for approximately 16 h. The reaction was quenched by the addition of basic alumina, and the resulting suspension was filtered through a short column of basic alumina eluting with EtOAc. The filtrate was concentrated in vacuo and the crude residue containing 1b was used without further purification in the subsequent reaction.

Workup

  1. customThe reaction was quenched by the addition of basic alumina
  2. filtrationthe resulting suspension was filtered through a short column of basic alumina eluting with EtOAc
  3. concentrationThe filtrate was concentrated in vacuo
  4. additionthe crude residue containing 1b
  5. customwas used without further purification in the subsequent reaction

Sources & evidence

ORD record
ord-07cd860a354d4f5986007bdbc01d2524
Source dataset
uspto-grants-2013_04
Patent number
US08426413B2

Reaction notes

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