Toluene → HCID 57910788, compound

HRID 1644864Notes

Reaction equation

HRID 1644864 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-270addf0d7474d258dfc689bd7447cd0
Source dataset
uspto-grants-2012_02
Patent number
US08124628B2

Reaction notes

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