Diethyl Ether → 2H-Indeno[2,1-d]oxazol-2-one, 3,3a,4,8b-tetrahydro-, cis-

HRID 965226Notes

Reaction equation

HRID 965226 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]C(C)(C)C)=[O:13].C(OCC)C>C(Cl)(Cl)Cl>[O:13]1[C@H:2]2[C:10]3[C:5]([CH2:4][C@H:3]2[NH:11][C:12]1=[O:14])=[CH:6][CH:7]=[CH:8][CH:9]=3

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 18661305(+/-)trans-1-Chloro-2-tert-butoxycarbonylaminoindane

Product 1

HCID 867528562H-Indeno[2,1-d]oxazol-2-one, 3,3a,4,8b-tetrahydro-, cis-Yield 92.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of (±) trans-1-chloro-2-tert-butoxycarbonylaminoindane (10.0 g, 0.037 mol) in chloroform (200 ml) was heated under reflux in an argon atmosphere for 23 h. The mixture was concentrated in vacuo to give a brown solid. Trituration with diethyl ether afforded the title compound as a beige solid (6.0 g, 92%) m.p. 205°-206° C. which was used without further purification.

Workup

  1. temperatureunder reflux in an argon atmosphere for 23 h
  2. concentrationThe mixture was concentrated in vacuo
  3. customto give a brown solid

Sources & evidence

ORD record
ord-5b8611b88a6e4c3d9cd3615833de6fae
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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