Diethyl chlorophosphate → HCID 53434223, compound

HRID 1011839Notes

Reaction equation

HRID 1011839 reaction equation
C([N-]C(C)C)(C)C.[Li+].C(O[CH2:14][C:15]([C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)=O)CCC.P(Cl)(OCC)([O:29][CH2:30][CH3:31])=O>O1CCCC1>[C:15]([C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[O:29][CH2:30][CH3:31])#[CH:14]

Participants

5

Reactant 3

HCID 13139Diethyl chlorophosphateHCID 2724682Lithium diisopropylamide2×HCID 67314946HCID 67314946, compound

Product 1

HCID 53434223HCID 53434223, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, 9.19 ml of 2 mol/l tetrahydrofuran solution of lithium diisopropyl amide was added dropwise to 3.3 g of 2-butoxyacetonaphthone at −78° C., and the mixture was stirred for 2 hours. After addition of 3.17 g of diethyl chlorophosphate, the mixture was stirred at room temperature for 1 hour. 2.65 ml of 2 mol/l tetrahydrofuran solution of lithium diisopropyl amide was added dropwise thereto at −78° C., and the mixture was stirred for 18 hours. The compounds obtained were extracted with added ethyl ether. The ethyl ether layer was washed twice with 300 ml of distilled water, dried over anhydrous magnesium sulfate for 24 hours and filtered, and the solvent was evaporated. The residue was subjected to column purification by using chloroform/hexane (1/4) as the developing solvent, to give 1.9 g of 1-ethynyl-2-ethoxynaphthalene.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. stirringat −78° C., and the mixture was stirred for 18 hours
  3. customThe compounds obtained
  4. extractionwere extracted with added ethyl ether
  5. washThe ethyl ether layer was washed twice with 300 ml of distilled water
  6. dry with materialdried over anhydrous magnesium sulfate for 24 hours
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was subjected to column purification

Sources & evidence

ORD record
ord-289d6962202e4eb1adb0d9636fa9be02
Source dataset
uspto-grants-2011_07
Patent number
US07977441B2

Reaction notes

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