p-Toluenesulfonic acid monohydrate → HCID 66815740, 화합물

HRID 2367927노트

반응식

HRID 2367927 반응식
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

참가 물질

5

반응물 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21226206Ethyl acetate hexaneHCID 66815652HCID 66815652, 화합물

생성물 1

HCID 66815740HCID 66815740, 화합물수율 65.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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)+

후처리

  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)

출처 및 근거

ORD 기록
ord-032bf06ef2fc4139984137dd3474e03b
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703700B2

반응 노트

불러오는 중…