Water → Naphthalene, 1,2,3,4-tetrahydro-1-methylene-

HRID 366380Notes

Reaction equation

HRID 366380 reaction equation
[I-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:22]1[CH2:32][C:30](=O)[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23]1.O>C1COCC1>[CH2:2]=[C:30]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22][CH2:32]1

Participants

5

Reactant 3

HCID 962WaterHCID 107241-TetraloneHCID 638159Methyltriphenylphosphonium iodide

Product 1

HCID 141173Naphthalene, 1,2,3,4-tetrahydro-1-methylene-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-Butyl lithium (Aldrich) (47 cm3, 74.8 mmol, 1.6 M solution in hexane) was added dropwise to a solution of methyl triphenylphosphonium iodide (Aldrich) (27.65 g, 68 mmol) in dry THF (150 cm3), under nitrogen at 0° C. α-Tetralone (Aldrich) (10 g, 68 mmol) in dry THF (100 cm3 was then added dropwise and the mixture stirred for 17 hours at room temperature. The reaction mixture was then added to water and extracted with ethyl acetate. The combined extracts were then dried (Na2SO4), filtered and concentrated in vacuo. Purification was by column chromatography on a neutralised silica column (Et3N) (Eluant: Pet. Ether 40-60° C.) produced a colourless mobile oil.

Workup

  1. additionwas then added dropwise
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined extracts were then dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification
  7. customwas by column chromatography on a neutralised silica column (Et3N) (Eluant: Pet. Ether 40-60° C.)
  8. customproduced a colourless mobile oil

Sources & evidence

ORD record
ord-64f9ec1362ec4bfbbaa76aa8642de618
Source dataset
uspto-grants-2000_10
Patent number
US06130228

Reaction notes

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