Hexane → HCID 23114103, compound

HRID 1787133Notes

Reaction equation

HRID 1787133 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.[OH:22][C:23]1[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([CH3:32])[C:24]=1[CH:25]=[O:26]>C1COCC1.O>[OH:26][CH:25]([C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:4][CH:3]=1)[C:24]1[C:27]([CH3:32])=[CH:28][C:29]([CH3:31])=[CH:30][C:23]=1[OH:22]

Participants

7

Reactant 4

HCID 8058HexaneHCID 114621-Bromo-4-isopropylbenzeneHCID 591070HCID 591070, compoundHCID 178418339Butyllithium

Product 1

HCID 23114103HCID 23114103, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-bromo-4-isopropylbenzene (3.32 g, 16.7 mmol) in THF (30 mL) was added dropwise n-butyllithium (a 1.59 M hexane solution, 9.2 mL, 14.7 mmol) under argon atmosphere at −78° C. The reaction solution was stirred for 30 minutes, a solution of 2-hydroxy-4,6-dimethylbenzaldehyde obtained in Reference Example 146 (1.0 g, 6.7 mmol) in THF (10 mL) was added dropwise thereto at −78° C., and the mixture then was stirred for 30 minutes. The reaction solution was warmed to room temperature, water was added thereto to separate the organic layer, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with a saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2) to obtain 1.64 g (yield 91%) of the title compound. Melting point: 103-104° C. (ethyl acetate-hexane).

Workup

  1. additionwas added dropwise
  2. stirringat −78° C., and the mixture then was stirred for 30 minutes
  3. customto separate the organic layer
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layer was washed with a saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-a8ec02a46067491c9fcf32a61bc6e041
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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