Diethyl Ether → Cyclohexanol, 1-ethynyl-, 1-acetate

HRID 270441

反応式

HRID 270441 の反応式
[C:1]([C:3]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[CH:2].[C:10](OC(=O)C)(=[O:12])[CH3:11].C([O-])(O)=O.[Na+].CCOCC>C(#N)C.C1COCC1.[O-]S(C(F)(F)F)(=O)=O.[Sc+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>[C:10]([O:9][C:3]1([C:1]#[CH:2])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)(=[O:12])[CH3:11]

参加物

8

反応物 4

HCID 3283Diethyl EtherHCID 65251-EthynylcyclohexanolHCID 7918Acetic AnhydrideHCID 516892Sodium Bicarbonate

生成物 1

HCID 78903Cyclohexanol, 1-ethynyl-, 1-acetate収率 110.7%

試薬・触媒・溶媒 3

HCID 2734571Scandium(III) triflate触媒2 回HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To 3.1 g (25 mmol) 1-ethynyl-1-cyclohexanol in 25 ml acetonitrile were added 7.1 ml (75 mmol, 3 eq) acetic anhydride at −20° C. 12.3 mg (0.03 mmol) scandiumtriflate in 300 μl THF were added and the solution was stirred for 2 h. Additional 12.3 mg (0.03 mmol) scandiumtriflate in 300 μl THF were added and stirring was continued for 30 min. A saturated aqueous solution of NaHCO3 and ether were added. The layers were separated and the inorganic one was extracted with ether. The combined organic phases were washed with brine and dried over Na2SO4. Evaporation yielded 4.6 g crude 1-ethynylcyclohexyl acetate as colorless oil, MS: 166 (M).

後処理

  1. stirringstirring
  2. waitwas continued for 30 min
  3. customThe layers were separated
  4. extractionthe inorganic one was extracted with ether
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over Na2SO4
  7. customEvaporation

出典と根拠

ORDレコード
ord-a67f1e0cc08c4f6a98f30aa3663cf99f
出典データセット
uspto-grants-2008_11
特許番号
US07449483B2

関連ノート

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