Citric Acid → (1RS,4RS)-3-ethyl-4-methyl-4-methoxymethoxy-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether

HRID 582744노트

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HRID 582744 반응식
[Si:1]([O:8][CH:9]1[CH2:13][C:12]([CH3:15])([OH:14])[C:11]([CH2:16][CH3:17])=[CH:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[CH3:27][O:28][CH2:29]Cl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)(Cl)Cl>[Si:1]([O:8][CH:9]1[CH2:13][C:12]([CH3:15])([O:14][CH2:27][O:28][CH3:29])[C:11]([CH2:16][CH3:17])=[CH:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 57032808(1RS,4RS)-3-ethyl-4-methyl-4-hydroxy-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether

생성물 1

HCID 57024402(1RS,4RS)-3-ethyl-4-methyl-4-methoxymethoxy-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether수율 95%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution mixture of 2.1 g of (1RS,4RS)-3-ethyl-4-methyl-4-hydroxy-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether, 2.7 g of N,N-diisopropylethylamine and 30 ml of chloroform was added under ice-cooling 1.24 ml of chloromethyl methyl ether, and the resulting mixture was allowed to react at room temperature for 8 hours. Then the reaction liquid was poured into ice-cooled 5% aqueous solution of citric acid and extracted two times with diethyl ether. The combined ether layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 2.35 g of (1RS,4RS)-3-ethyl-4-methyl-4-methoxymethoxy-2-cyclopenten-1-yl (t-butyldimethylsilyl) ether. Yield 95%

후처리

  1. additionwas added under ice-
  2. customto react at room temperature for 8 hours
  3. customThen the reaction liquid
  4. additionwas poured into ice-
  5. extractionextracted two times with diethyl ether
  6. washThe combined ether layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue thus obtained

출처 및 근거

ORD 기록
ord-f7381d70ffc84850931d05ce52b8e9e3
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05925676

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