Potassium Carbonate → HCID 59832103, compound

HRID 268696Notes

Reaction equation

HRID 268696 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][C:32]1[N:33]=[C:34]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[O:35][C:36]=1[CH3:37])(=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][C:32]3[N:33]=[C:34]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[O:35][C:36]=3[CH3:37])=[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 105407732-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethyl methanesulfonateHCID 59832111Tert-butyl 7-hydroxychromane-3-carboxylate

Product 1

HCID 59832103HCID 59832103, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of tert-butyl 7-hydroxychromane-3-carboxylate (2.5 g, 10 mmol) in CH3CN (20 ml), K2CO3 (4.1 g) and 2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethyl methanesulfonate (3.7 g) were added and the reaction mixture was heated under reflux for overnight. The reaction mixture was cooled to room temperature and diluted with 100 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 (2.8 g, 64.3%).

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-16560c2b37214c55b0d4b8e7ede14f83
Source dataset
uspto-grants-2008_11
Patent number
US07446127B2

Reaction notes

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