4-Methoxymandelic acid → 2-Trimethylsilylethyl 4-methoxymandelate

HRID 1534093ノート

反応式

HRID 1534093 の反応式
[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

参加物

5

反応物 2

HCID 1120564-Methoxymandelic acidHCID 178457954HCID 178457954、化合物

生成物 1

HCID 137057282-Trimethylsilylethyl 4-methoxymandelate収率 72%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-037917923f3e438fbf6b7a03f3e88f07
出典データセット
uspto-grants-1992_02
特許番号
US05087631

反応ノート

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