Citric Acid → 2-[1-[2-(3,5-Diacetoxymethylphenyoxy)ethyl]cyclohexyl]ethanol

HRID 2223910ノート

反応式

HRID 2223910 の反応式
[O:1]([CH2:19][CH2:20][C:21]1([CH2:27][CH2:28][O:29][C:30]2[CH:35]=[C:34]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[CH:33]=[C:32]([CH2:41][O:42][C:43](=[O:45])[CH3:44])[CH:31]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[C:38]([O:37][CH2:36][C:34]1[CH:35]=[C:30]([O:29][CH2:28][CH2:27][C:21]2([CH2:20][CH2:19][OH:1])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[CH:31]=[C:32]([CH2:41][O:42][C:43](=[O:45])[CH3:44])[CH:33]=1)(=[O:40])[CH3:39]

参加物

5

反応物 3

HCID 311Citric AcidHCID 11078149TBAF tetrahydrofuranHCID 691465871-[2-[1-[2-(Tert-butyldiphenylsiloxy)ethyl]cyclohexyl]ethoxy]-3,5-diacetoxymethylbenzene

生成物 1

HCID 597148422-[1-[2-(3,5-Diacetoxymethylphenyoxy)ethyl]cyclohexyl]ethanol収率 62.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-[2-[1-[2-(tert-butyldiphenylsiloxy)ethyl]cyclohexyl]ethoxy]-3,5-diacetoxymethylbenzene (1.13 g) dissolved in tetrahydrofuran (7 mL) was added a 1M tetrabutylammonium fluoride/tetrahydrofuran solution (2.8 mL) dropwise at room temperature. The solution was stirred for 15 hours. A 10% aqueous citric acid solution was added to the solution, and it was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was then concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, hexane:ethyl acetate (1:1)] to give the title compound (439 mg).

後処理

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was then concentrated under reduced pressure
  6. customThe resulting residue was purified by chromatography [silica gel, hexane:ethyl acetate (1:1)]

出典と根拠

ORDレコード
ord-d06f058558e0464c92bac6474ccdea20
出典データセット
uspto-grants-2008_05
特許番号
US07375115B2

反応ノート

読み込み中…