Potassium Carbonate → Tert-butyl-7-[(2-phenyl-5-methyl-1,3-oxazol-4-yl)methoxy]chromane-3-carboxylate

HRID 268699Notes

Reaction equation

HRID 268699 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].C(=O)([O-])[O-].[K+].[K+].[OH:21][C:22]1[CH:31]=[C:30]2[C:25]([CH2:26][CH:27]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][O:29]2)=[CH:24][CH:23]=1>O>[C:35]([O:34][C:32]([CH:27]1[CH2:26][C:25]2[C:30](=[CH:31][C:22]([O:21][CH2:2][C:3]3[N:4]=[C:5]([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[O:6][C:7]=3[CH3:8])=[CH:23][CH:24]=2)[O:29][CH2:28]1)=[O:33])([CH3:38])([CH3:36])[CH3:37]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazoleHCID 59832111Tert-butyl 7-hydroxychromane-3-carboxylate

Product 1

HCID 69279834Tert-butyl-7-[(2-phenyl-5-methyl-1,3-oxazol-4-yl)methoxy]chromane-3-carboxylateYield 71.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 4-(chloromethyl)-5-methyl-2-phenyl-1,3-oxazole (103.5 mg, 0.5 mmol) and potassium carbonate (138.4 mg, 1 mmol), tert-butyl 7-hydroxychromane-3-carboxylate (125 mg, 0.5 mmol) was added and the reaction mixture was stirred at room temperature for 48 hrs. Water (50 ml) was added and the precipitated product was extracted with 25 ml of diethyl ether. Ether layer was washed with water (25 ml) twice and dried. On evaporation of solvent, the product was obtained as pale yellow gum (150 mg, 36%).

Workup

  1. extractionthe precipitated product was extracted with 25 ml of diethyl ether
  2. washEther layer was washed with water (25 ml) twice
  3. customdried
  4. customOn evaporation of solvent

Sources & evidence

ORD record
ord-8312fd09f0f741928d9a29f2500a4296
Source dataset
uspto-grants-2008_11
Patent number
US07446127B2

Reaction notes

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