Dimethylformamide → HCID 54507751, compound

HRID 1166728Notes

Reaction equation

HRID 1166728 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][CH2:13][O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)=[CH:4][CH:3]=1.C([Li])CCC.CN([CH:29]=[O:30])C>C1COCC1.CCCCCC>[CH:29]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][CH2:13][O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)=[CH:4][CH:3]=1)=[O:30]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 53778239HCID 53778239, compoundHCID 178418339Butyllithium

Product 1

HCID 54507751HCID 54507751, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 1-bromo-4-(2-tetrahydropyranyloxyethyl)naphthalene in anhydrous THF (15 mL) under nitrogen was cooled to −78° C. n-Butyl lithium (1.4 mL of a 2.5 M solution in hexane) was added via syringe, and the mixture was stirred at the same temperature for 30 min. DMF (1.1 mL) was added, and the mixture was allowed to reach room temperature. It was diluted with satd. NH4Cl solution (10 mL), extracted with ether (3×10 ml), dried (MgSO4) and concentrated. Flash chromatography using hexane/ethyl acetate 5:1 as eluent provided 408 mg (54%) of a colorless oil.

Workup

  1. additionwas added via syringe
  2. customto reach room temperature
  3. additionIt was diluted with satd
  4. extractionNH4Cl solution (10 mL), extracted with ether (3×10 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-36219b978a7142269ca9c040ff2de540
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

Loading…