Trifluoroacetic acid → HCID 21938232, compound

HRID 2187748Notes

Reaction equation

HRID 2187748 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH3:14])=[CH:8]2)=[O:4].[CH2:15]([O:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C.[OH-].[Na+]>C(Cl)Cl>[CH2:15]([O:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:27][C:8]2[C:7]3[C:11](=[CH:12][CH:13]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=3)[NH:10][C:9]=2[CH3:14])=[CH:29][CH:30]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 12230324HCID 12230324, compound

Product 1

HCID 21938232HCID 21938232, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A methylene chloride (15 ml) solution of 5-(methoxycarbonyl)-2-methylindole (0.567 g) and 4-benzyloxybenzaldehyde (0.700 g) is dropwise added to a methylene chloride (15 ml) solution of trifluoroacetic acid (0.513 g) and triethylsilane (1.047 g) in an ice-water bath, over a period of 15 minutes. This is stirred for 30 minutes in the ice-water bath, and an aqueous solution of 2 M sodium hydroxide is added thereto to stop the reaction. The organic layer is washed with a saturated saline solution, dried and concentrated. The resulting residue is purified through silica gel column chromatography (eluent: ethyl acetate/hexane=3/7) to obtain 3-(4-benzyloxybenzyl)-5-(methoxycarbonyl)-2-methylindole (62) (0.510 g).

Workup

  1. customthe reaction
  2. washThe organic layer is washed with a saturated saline solution
  3. customdried
  4. concentrationconcentrated
  5. customThe resulting residue is purified through silica gel column chromatography (eluent: ethyl acetate/hexane=3/7)

Sources & evidence

ORD record
ord-985632ee93ca4f21ba7fff977b2e6655
Source dataset
uspto-grants-2002_06
Patent number
US06410584B1

Reaction notes

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