Diethyl Ether → HCID 10942917, compound

HRID 2269347Notes

Reaction equation

HRID 2269347 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14]COCC.[OH-].[Na+]>C1COCC1.[CH3-].C[Al+]C.[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Cl-].[Ti+3]>[C:1]1([CH:7]2[CH2:12][CH2:11][C:10](=[CH2:14])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 786054-Phenylcyclohexanone

Product 1

HCID 10942917HCID 10942917, compoundYield 61%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
25 °C

Procedure

μ-Chloro-μ-methylene[bis(cyclopentadienyl)titanium]dimethylaluminum (172 mL, 0.086 mol, 0.5 M in toluene) is added dropwise to a solution of 4-phenylcyclohexanone (15.0 g, 0.086 mol) in THF (100 mL) at 0° C. The mixture is allowed to come to 25° C. After 15 min., ether (100 mL) is added followed by dropwise addition of 0.1 M sodium hydroxide (120 mL). The mixture is stirred an 25° C. for 18 h, filtered, and the filtrate is dried over sodium sulfate and concentrated in vacuo . The residue is purified by column chromatography on silica gel using dichloromethane-hexanes (1:1) as eluent. The resulting yellow oil is rechromatographed using hexanes as eluent to give 8.9 g (61%) of 4-phenyl-1-methylenecyclohexane as an oil.

Workup

  1. customto come to 25° C
  2. filtrationfiltered
  3. dry with materialthe filtrate is dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by column chromatography on silica gel
  6. customThe resulting yellow oil is rechromatographed

Sources & evidence

ORD record
ord-1abf9395dab24282b18428279602dc95
Source dataset
uspto-grants-2001_12
Patent number
US06329400B1

Reaction notes

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