Monobenzone → trans-1-(4-Benzyloxyphenoxy)-2-ethoxycarbonylaminoindane

HRID 965223Notes

Reaction equation

HRID 965223 reaction equation
[CH2:1]([O:3][C:4]1[O:5][C@H:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][C@H:7]2[N:8]=1)[CH3:2].[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(C)C=CC=CC=1.C(OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:16]([O:23][C:24]1[CH:25]=[CH:26][C:27]([O:30][C@@H:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][C@H:7]2[NH:8][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:28][CH:29]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 2

HCID 7638MonobenzoneHCID 18661302(3AR,8bS)-2-ethoxy-4,8b-dihydro-3aH-indeno[2,1-d]oxazole

Product 1

HCID 18661303trans-1-(4-Benzyloxyphenoxy)-2-ethoxycarbonylaminoindaneYield 26.9%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

(±) cis-2-Ethoxy-3a,8b-dihydro-4H-indeno[2,1-d]oxazole (2.2 g, 10.8 mmol), 4-benzyloxyphenol (2.17 g, 10.8 mmol), p-toluenesulfonic acid (40 mg) were dissolved in toluene (50 ml) and heated at 60° C. for 5 h, then 2 h at reflux under nitrogen. On cooling, the reaction mixture was diluted with diethyl ether (150 ml) and washed sequentially with 10% aq. sodium hydroxide, water and brine. After drying over sodium sulfate, solvents were removed in vacuo and the residue subjected to column chromatography on silica gel eluting with 20% diethyl ether in hexanes to afford the title compound (1.17 g) as a foam.

Workup

  1. temperature2 h at reflux under nitrogen
  2. temperatureOn cooling
  3. washwashed sequentially with 10% aq. sodium hydroxide, water and brine
  4. dry with materialAfter drying over sodium sulfate, solvents
  5. customwere removed in vacuo

Sources & evidence

ORD record
ord-f10091b9cc5a4eeab2b547877da94738
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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