Water → HCID 22327806, compound

HRID 271003Notes

Reaction equation

HRID 271003 reaction equation
[CH3:1][C:2]([CH2:8][CH:9]([CH3:11])[CH3:10])=[C:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1.[CH3:12][Li].O>CCOCC>[CH3:1][C:2]([C:3]1[CH2:7][CH:6]=[CH:5][CH:4]=1)([CH3:12])[CH2:8][CH:9]([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 5626186-Methyl-6-isobutylfulveneHCID 178418348HCID 178418348, compound

Product 1

HCID 22327806HCID 22327806, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 8.00 g (54.0 mmol) of 6-methyl-6-isobutylfulvene in 30 ml of ether, 54.0 ml (61.6 mmol) of an ether solution of methyllithium was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for 4 days. Then, 30 ml of water was added. The separated organic phase was washed with water and a saturated saline solution, then dried over magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was subjected to vacuum distillation (120° C./25 mmHg) to obtain 7.10 g (43.2 mmol) of a light yellow liquid (yield: 80%)

Workup

  1. washThe separated organic phase was washed with water
  2. dry with materiala saturated saline solution, then dried over magnesium sulfate
  3. filtrationfiltered
  4. customFrom the filtrate, the solvent was removed under reduced pressure
  5. customto obtain a liquid
  6. distillationThe liquid was subjected to vacuum distillation (120° C./25 mmHg)

Sources & evidence

ORD record
ord-911eee3c27904bc59bc847f14493b0c2
Source dataset
uspto-grants-2008_11
Patent number
US07449533B2

Reaction notes

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