Ammonium Chloride → 2-Benzoyloxymethyl-4-hydroxymethylbenzyl benzoate

HRID 584290노트

반응식

HRID 584290 반응식
[C:1]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][O:18][Si](C(C)(C)C)(C)C)=[CH:13][C:12]=1[CH2:26][O:27][C:28](=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>C(OCC)(=O)C>[C:1]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][C:12]=1[CH2:26][O:27][C:28](=[O:35])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 697935022-Benzoyloxymethyl-4-(tert-butyldimethylsilanyloxymethyl)benzyl benzoate

생성물 1

HCID 697922262-Benzoyloxymethyl-4-hydroxymethylbenzyl benzoate수율 88.4%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

69 g (140 mmol) of 2-benzoyloxymethyl-4-(tert-butyldimethylsilanyloxymethyl)benzyl benzoate are placed in 450 ml of ethyl acetate in a round-bottomed flask and under a stream of nitrogen. 178 ml of tetrabutylammonium fluoride (1M/THF) are added. The medium is stirred for 30 minutes at room temperature. It is then poured into saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and then evaporated. The residue is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (40/60) to give 46.6 g (88%) of the expected product in the form of a white powder with a melting point of 92° C.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is purified by chromatography on a column of silica
  6. washeluted with a mixture of heptane and ethyl acetate (40/60)

출처 및 근거

ORD 기록
ord-50c318bd534c4327a3ed0a4616720d6c
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06924400B2

반응 노트

불러오는 중…