Potassium Carbonate → (3AR,8bS)-2-ethoxy-4,8b-dihydro-3aH-indeno[2,1-d]oxazole

HRID 965205Notes

Reaction equation

HRID 965205 reaction equation
Cl[C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]1[NH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C([O-])([O-])=O.[K+].[K+]>C(O)C.O>[CH2:15]([O:14][C:12]1[O:13][C@H:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][C@H:3]2[N:11]=1)[CH3:16]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 7070371trans-1-Chloro-2-ethoxycarbonylaminoindane

Product 1

HCID 18661302(3AR,8bS)-2-ethoxy-4,8b-dihydro-3aH-indeno[2,1-d]oxazole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of (±) trans-1-chloro-2-ethoxycarbonylaminoindane (B. J. Walker and P. J. Wrobel, J. Chem. Soc. Chem. Commun., 1980, 462)(4.0 g, 0.017 mol) in ethanol (125 ml) was treated with K2CO3 (2.4 g, 0.018 mol) and diluted with water (50 ml). After stirring at room temperature for 20 h, the reaction was concentrated under high vacuum to approximately one quarter the original volume, then diluted with water (25 ml) and extracted into diethyl ether (3×50 ml). The combined extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo to give the title compound as a low melting solid (3.3 g), m.p 53°-54° C. (from diethyl ether/n-pentane).

Workup

  1. concentrationthe reaction was concentrated under high vacuum to approximately one quarter the original volume
  2. additiondiluted with water (25 ml)
  3. extractionextracted into diethyl ether (3×50 ml)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-99d327fa069d422fadc2dd1db8ddd58a
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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