4-Methoxymandelic acid → 2-Trimethylsilylethyl 4-methoxymandelate

HRID 1534093노트

반응식

HRID 1534093 반응식
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]([OH:11])[C:8]([OH:10])=[O:9])=[CH:5][CH:4]=1.[CH3:14][Si:15]([CH3:29])([CH3:28])[CH2:16][CH2:17]N=C(O)N(C(C)C)C(C)C>O1CCOCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:7]([OH:11])[C:8]([O:10][CH2:17][CH2:16][Si:15]([CH3:29])([CH3:28])[CH3:14])=[O:9])=[CH:12][CH:13]=1

참가 물질

5

반응물 2

HCID 1120564-Methoxymandelic acidHCID 178457954HCID 178457954, 화합물

생성물 1

HCID 137057282-Trimethylsilylethyl 4-methoxymandelate수율 72%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of 4-methoxymandelic acid (2.00 g, 10.978 mmol) in 55 mL of dioxane at 90° C. is added 2-trimethylsilylethyl-N,N-diisopropyl-pseudourea. The resulting solution is refluxed for about 8 hours. After cooling the mixture is diluted with 50 mL of ethyl acetate, filtered, washed with saturated aqueous sodium bicarbonate followed by brine, dried over magnesium sulfate, and concentrated. The resulting residue is chromatographed on silica gel (9/1 hexanes/ethyl acetate) to give the title compound as an oil: 2.24 g, 72% yield. 1H NMR (300 MHz, CDCl3): 7.32 (d, J=8.8, 2 H), 6.89 (d, J=8.8, 2 H), 5.08 (d, J=5.6, 1 H), 4.38-4.17 (m, 2 H), 3.81 (s, 3 H), 3.41 (d, J=5.6, 1 H), 0.96 (m, 2 H), 0.01 (s, 9 H).

후처리

  1. temperatureThe resulting solution is refluxed for about 8 hours
  2. temperatureAfter cooling the mixture
  3. filtrationfiltered
  4. washwashed with saturated aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue is chromatographed on silica gel (9/1 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-037917923f3e438fbf6b7a03f3e88f07
출처 데이터셋
uspto-grants-1992_02
특허 번호
US05087631

반응 노트

불러오는 중…