Diethyl Ether → 1,1-Diphenylacetone

HRID 864492

反応式

HRID 864492 の反応式
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17]([Sn](CCCC)(CCCC)COCC1C=C(C(F)(F)F)C=C(C(F)(F)F)C=1)CCC.C(OCC)C.[F-].[K+]>C(Cl)(Cl)Cl>[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](=[O:9])[CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 746372,2-Diphenylacetyl chlorideHCID 522689Potassium FluorideHCID 85682165Tri-n-butyl-((3,5-bis(trifluoromethyl)phenyl)methyloxymethyl)tin

生成物 1

HCID 699071,1-Diphenylacetone

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
80 °C

実験手順

Diphenylacetyl chloride (4.6 g), tri-n-butyl-((3,5-bis(trifluoromethyl)phenyl)methyloxymethyl)tin (12.6 g; Example 1a, (Method Ai)and benzylchlorobis(triphenylphosphine) palladium (II)(80 mg)were dissolved in chloroform (10 ml) and the solution heated at 80° C. for 6h. On cooling diethyl ether and saturated aqueous potassium fluoride were added and after 30 minutes the solution was filtered through Hiflo™. The organic layer was washed with water, saturated brine and dried (MgSO4). After evaporation in vacuo the residual oil was purified by chromatography on silica gel (eluting with 0 to 10% ethyl acetate in petroleum ether bp=60°-80° C.) to give 1-(3,5-bis(trifluoromethyl)phenyl)methyloxy)-3,3-diphenyl acetone as an oil. 1H NMR (CDCl3, 360MHz) δ7.80 (1H; s; 4-aryl CH) 7.71 (2H; s; 2,6-aryl CH), 7.43-7.24 (10H; m; phenyl), 5.30 (1H; s; Ph2CH), 4.56 (2H; s), 4.31 (2H; s). m/e Found 452.1191, C24H13F6O2 requires 452.12110.

後処理

  1. additionwere added and after 30 minutes the solution
  2. filtrationwas filtered through Hiflo™
  3. washThe organic layer was washed with water, saturated brine
  4. dry with materialdried (MgSO4)
  5. customAfter evaporation in vacuo the residual oil
  6. customwas purified by chromatography on silica gel (eluting with 0 to 10% ethyl acetate in petroleum ether bp=60°-80° C.)

出典と根拠

ORDレコード
ord-cfa0d90d320c4607a1d2e6bcdc8c5fd8
出典データセット
uspto-grants-1996_10
特許番号
US05563161

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