1,1'-(Diazomethylene)bis(benzene) → Diphenylmethyl 2-(9-benzyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indol-2-yl)acetate

HRID 1417485Notes

Reaction equation

HRID 1417485 reaction equation
[C:1]1([C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N+]=[N-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16]([N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]2[CH2:32][CH2:33][CH:34]([CH2:36][C:37]([OH:39])=[O:38])[S:35][C:24]1=2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(OCC)(=O)C>[CH2:16]([N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]2[CH2:32][CH2:33][CH:34]([CH2:36][C:37]([O:39][CH:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:38])[S:35][C:24]1=2)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 545749702-(9-Benzyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indol-2-yl) acetic acid

Product 1

HCID 53637674Diphenylmethyl 2-(9-benzyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indol-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

An excess of diphenyldiazomethane was added to a mixture of 100 mg of 2-(9-benzyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indol-2-yl)acetic acid (prepared as described in Example 83) in 5 ml of ethyl acetate, with stirring, at room temperature, and stirring was continued at this temperature overnight. At the end of this time, the solvent was removed by evaporation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using a mixture of 6% v/v ethyl acetate in hexane as the eluent, to afford 139 mg of the title compound as an oil.

Workup

  1. stirringstirring
  2. customwas continued at this temperature overnight
  3. customAt the end of this time, the solvent was removed by evaporation under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography
  5. additiona mixture of 6% v/v ethyl acetate in hexane as the eluent

Sources & evidence

ORD record
ord-3df44a468f854d93bf55e629fbcb8b7e
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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