Tetrahydrofuran → 2-Decyl-6-methoxynaphthalene

HRID 1476362Notes

Reaction equation

HRID 1476362 reaction equation
C1COCC1.[CH2:6]([Mg]Br)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C(Br)CCCCCCCCC.Br[C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[CH:36]=[C:35]([O:40][CH3:41])[CH:34]=[CH:33]2>O.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:6]([C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[CH:36]=[C:35]([O:40][CH3:41])[CH:34]=[CH:33]2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 81731-BromodecaneHCID 787862-Bromo-6-methoxynaphthaleneHCID 178418384HCID 178418384, compound

Product 1

HCID 867043812-Decyl-6-methoxynaphthalene

Reagents, catalysts & solvents 2

HCID 178418745HCID 178418745, compoundCatalystHCID 962WaterSolvent

Procedure

A THF solution of n-decyl magnesium bromide (prepared as a THF (2 ml) solution of n-decyl bromide (2.2 ml, 11 mmol) and Mg (292 mg, 12 mmol)) was added to 6-bromo-2-methoxynaphthalene (2.37 g, 10 mmol) easily available from a reagent manufacturer and a THF (10 ml) solution of Ni(dppp)Cl2 (271 mg, 0.5 mmol), and the mixture was heated under reflux for 19 hours. After cooling, the mixed solution was diluted with water (10 ml), and non-reacted Mg was filtered out. The filtered solution was extracted with ether (5 ml×3). The extracted organic phases were collected (10 ml×3), and dried with MgSO4, and condensed with an evaporator. The condensed organic phase was recrystallized with hexane to obtain 6-n-decyl-2-methoxynaphthalene (compound (3)-64) as a light yellow solid.

Workup

  1. temperatureunder reflux for 19 hours
  2. temperatureAfter cooling
  3. filtrationwas filtered out
  4. extractionThe filtered solution was extracted with ether (5 ml×3)
  5. customThe extracted organic phases were collected (10 ml×3)
  6. dry with materialdried with MgSO4, and condensed with an evaporator
  7. customThe condensed organic phase was recrystallized with hexane

Sources & evidence

ORD record
ord-0a539def97724f5f858adcdbbc2c0a6c
Source dataset
uspto-grants-2015_04
Patent number
US09018630B2

Reaction notes

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