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

HRID 268698Notes

Reaction equation

HRID 268698 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-851904e3997046e49449dfc1c85d22fa
Source dataset
uspto-grants-2008_11
Patent number
US07446127B2

Reaction notes

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