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Potassium Carbonate → Tert-butyl-7-[2-(5-methyl-2-thien-2-yl-1,3-oxazol-4-yl)ethoxy]chromane-3-carboxylic acid

HRID 268698
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HRID 268698 반응식
CS([O:5][CH2:6][CH2:7][C:8]1[N:9]=[C:10]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[O:11][C:12]=1[CH3:13])(=O)=O.O[C:20]1[CH:29]=[C:28]2[C:23]([CH2:24][CH:25]([C:30]([O:32]C(C)(C)C)=[O:31])[CH2:26][O:27]2)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CC#N.C(OCC)C>[C:23]([CH:26]1[CH:25]([C:30]([OH:32])=[O:31])[CH2:24][C:23]2[C:28](=[CH:29][C:20]([O:5][CH2:6][CH2:7][C:8]3[N:9]=[C:10]([C:14]4[S:15][CH:16]=[CH:17][CH:18]=4)[O:11][C:12]=3[CH3:13])=[CH:21][CH:22]=2)[O:27]1)([CH3:28])([CH3:24])[CH3:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 59832111Tert-butyl 7-hydroxychromane-3-carboxylateHCID 867607402-(5-Methyl-2-thien-2-yl-1,3-oxazol-4-yl)ethyl methanesulfonate

생성물 1

HCID 69279798Tert-butyl-7-[2-(5-methyl-2-thien-2-yl-1,3-oxazol-4-yl)ethoxy]chromane-3-carboxylic acid

시약·촉매·용매 2

HCID 3283Diethyl Ether용매
HCID 6342
Acetonitrile
용매

실험 절차

2-(5-methyl-2-thien-2-yl-1,3-oxazol-4-yl)ethyl methanesulfonate (947 mg, 3.3 mmol), tert-butyl 7-hydroxychromane-3-carboxylate (750 mg, 3 mmol) and potassium carbonate (1.24 g, 9 mmol) were mixed in CH3CN and refluxed under N2 atmosphere overnight. After the completion of the reaction (TLC), the reaction mixture was cooled to room temperature and diluted with 30 ml of diethyl ether and passed through a small pad of silica. Silica was washed with 100 ml of ether and the ether solution was evaporated to give the product which was purified by column chromatography on silica using ethyl acetate and hexanes as eluent (699 mg, 53%).

후처리

  1. temperaturerefluxed under N2 atmosphere overnight
  2. customAfter the completion of the reaction (TLC)
  3. washSilica was washed with 100 ml of ether
  4. customthe ether solution was evaporated
  5. customto give the product which
  6. customwas purified by column chromatography on silica

출처 및 근거

ORD 기록
ord-851904e3997046e49449dfc1c85d22fa
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07446127B2

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