Potassium Carbonate → tert-butyl-7-[3-(5-Methyl-2-phenyl-4-oxazolyl)propoxy]chromane-3-carboxylate

HRID 268700Notes

Reaction equation

HRID 268700 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][O:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].CS(O[CH2:30][CH2:31][CH2:32][C:33]1[N:34]=[C:35]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[O:36][C:37]=1[CH3:38])(=O)=O>CC#N.C(OCC)C>[C:15]([O:14][C:12]([CH:7]1[CH2:6][C:5]2[C:10](=[CH:11][C:2]([O:1][CH2:30][CH2:31][CH2:32][C:33]3[N:34]=[C:35]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[O:36][C:37]=3[CH3:38])=[CH:3][CH:4]=2)[O:9][CH2:8]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 220878333-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)propyl methanesulfonateHCID 59832111Tert-butyl 7-hydroxychromane-3-carboxylate

Product 1

HCID 69279614tert-butyl-7-[3-(5-Methyl-2-phenyl-4-oxazolyl)propoxy]chromane-3-carboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of tert-butyl 7-hydroxychromane-3-carboxylate (250 mg, 1 mmol) in CH3CN (10 ml), K2CO3 (414 mg) and 3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl methanesulfonate (325 mg) were added and the reaction mixture was heated under reflux for overnight. The reaction mixture was cooled to room temperature and diluted with 30 mL of diethyl ether. The diluted solution was passed through a pad of silica and the silica was washed with more ether. The ether solution was evaporated to dryness and purified using silica chromatography. The product was isolated as a white sold (397 mg, 88%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for overnight
  3. washthe silica was washed with more ether
  4. customThe ether solution was evaporated to dryness
  5. custompurified
  6. customThe product was isolated as

Sources & evidence

ORD record
ord-f4b3c15d976d4c24b6e3b2b89e5cb375
Source dataset
uspto-grants-2008_11
Patent number
US07446127B2

Reaction notes

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