p-Toluenesulfonic acid monohydrate → HCID 66815740、化合物

HRID 2367927ノート

反応式

HRID 2367927 の反応式
O1CCCCC1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([C:21]2[N:26]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C.CCCCCC>CO>[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([C:21]2[N:26]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1

参加物

5

反応物 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21226206Ethyl acetate hexaneHCID 66815652HCID 66815652、化合物

生成物 1

HCID 66815740HCID 66815740、化合物収率 65.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of methyl 6-(3-(6-(tetrahydro-2H-pyran-2-yloxy)hexyloxy)phenyl) picolinate (12), (260 mg, 0.63 mmol) in methanol (1 mL) was added catalytic p-toluenesulfonic acid monohydrate (26 mg) and the mixture was stirred at RT for 2-4 h. The reaction was monitored by TLC (ethyl acetate:hexane 1:1). After completion the volatiles were removed in vacuo and the oily residue dissolved in ethyl acetate. The solution was washed with bicarbonate and brine, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by gradient flash chromatography (ethyl acetate:hexane) to provide 135 mg (65%) of 13. TLC Rf=0.34 (ethyl acetate:hexanes 1:1), MS m/z 330 (M+H)+

後処理

  1. customAfter completion the volatiles were removed in vacuo
  2. dissolutionthe oily residue dissolved in ethyl acetate
  3. washThe solution was washed with bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by gradient flash chromatography (ethyl acetate:hexane)

出典と根拠

ORDレコード
ord-032bf06ef2fc4139984137dd3474e03b
出典データセット
uspto-grants-2014_04
特許番号
US08703700B2

反応ノート

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