Methanesulfonic Acid → (Z)-ethyl 1-benzylidene-6-methoxy-2,3-dihydro-1H-inden-2-ylcarbamate

HRID 82880Notes

Reaction equation

HRID 82880 reaction equation
[CH2:1]([C:8]1(O)[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[CH2:10][CH:9]1[NH:19][C:20](=[O:24])[O:21][CH2:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(O)(=O)=O>C1(C)C=CC=CC=1>[CH:1](=[C:8]1/[CH:9]([NH:19][C:20](=[O:24])[O:21][CH2:22][CH3:23])[CH2:10][C:11]2[C:16]/1=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 66741247ethyl 1-benzyl-1-hydroxy-6-methoxy-2,3-dihydro-1H-inden-2-ylcarbamate

Product 1

HCID 68083713(Z)-ethyl 1-benzylidene-6-methoxy-2,3-dihydro-1H-inden-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of ethyl 1-benzyl-1-hydroxy-6-methoxy-2,3-dihydro-1H-inden-2-ylcarbamate (184 mg, 0.539 mmol) in toluene (4 ml) was added methanesulfonic acid (3.50 μl, 0.054 mmol) and stirred at room temperature over night. The solution was evaporated, re-dissolved in dichloromethane, washed with sodium bicarbonate and brine, dried over sodium bicarbonate and evaporated to dryness to obtain the desired (Z)-ethyl 1-benzylidene-6-methoxy-2,3-dihydro-1H-inden-2-ylcarbamate as a pale yellow oil. m=154 mg (88%)

Workup

  1. customThe solution was evaporated
  2. dissolutionre-dissolved in dichloromethane
  3. washwashed with sodium bicarbonate and brine
  4. dry with materialdried over sodium bicarbonate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-2e3e2926e2e24042a8a82ae6b88de723
Source dataset
uspto-grants-2014_09
Patent number
US08846743B2

Reaction notes

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