6-Chloroacetyl-1,4-benzodioxane → 6-(2-Chloro-ethyl)-2,3-dihydro-benzo[1,4]dioxine

HRID 456612Notes

Reaction equation

HRID 456612 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:8]2[O:9][CH2:10][CH2:11][O:12][C:7]=2[CH:6]=1)=O>FC(F)(F)C(O)=O.C([SiH](CC)CC)C>[Cl:1][CH2:2][CH2:3][C:5]1[CH:14]=[CH:13][C:8]2[O:9][CH2:10][CH2:11][O:12][C:7]=2[CH:6]=1

Participants

3

Reactant 1

HCID 27801786-Chloroacetyl-1,4-benzodioxane

Product 1

HCID 179812436-(2-Chloro-ethyl)-2,3-dihydro-benzo[1,4]dioxineYield 89.9%

Reagents, catalysts & solvents 1

HCID 131722655TFA triethylsilaneSolvent

Procedure

A solution of 2-chloro-1-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-ethanone (0.5 g) in trifluoroacetic acid/triethylsilane (4 ml/1.3 ml) was stirred overnight then partitioned between dichloromethane and dilute aqueous sodium bicarbonate solution. The organic extract was dried and evaporated to give a brown oil (0.42 g) This was chromatographed on silica eluting with a dichloromethane/petroleum ether gradient affording the product as a clear oil (0.23 g).

Workup

  1. customthen partitioned between dichloromethane and dilute aqueous sodium bicarbonate solution
  2. extractionThe organic extract
  3. customwas dried
  4. customevaporated

Sources & evidence

ORD record
ord-0edb55f393f0472da45d797001f78509
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Reaction notes

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