Water → HCID 21196697, compound

HRID 1066888Notes

Reaction equation

HRID 1066888 reaction equation
I([O-])(=O)(=O)=O.[Na+].[CH2:7]([CH:10]1[CH2:18][CH2:17][C:13]2[S:14][CH:15]=[CH:16][C:12]=2[C:11]1=[O:19])[CH:8]=C.[OH2:20]>[Os](=O)(=O)(=O)=O.O1CCOCC1>[O:19]=[C:11]1[C:12]2[CH:16]=[CH:15][S:14][C:13]=2[CH2:17][CH2:18][CH:10]1[CH2:7][CH:8]=[O:20]

Participants

6

Reactant 3

HCID 962WaterHCID 21196668HCID 21196668, compoundHCID 23667635Sodium periodate

Product 1

HCID 21196697HCID 21196697, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A 4.20 g of sodium periodate was added gradually to a mixture of 1.80 g of 5-allyl-4-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene, 25 mg of osmium tetraoxide, 15 ml of water and 45 ml of dioxane, while keeping the reaction mixture at 24 to 26° C., and then the mixture was stirred at room temperature for 3 hours. After extraction of the reaction mixture with ethyl acetate, the organic layers were combined, washed with 2% sodium thiosulfate aqueous solution, water and brine in that order and then dried with anhydrous magnesium sulfate. After removal of the drying agent, the solvent was concentrated under a reduced pressure, and the resulting residue was purified by a silica gel column chromatography to give 1.33 g of (4-oxo-4,5,6,7-tetrahydrobenzo[b]thiophen-5-yl)acetaldehyde. A 1.32 g of the aldehyde compound and 1.39 g of N-acetylethylenediamine were dissolved in 50 ml of toluene. Then, 10 mg of camphorsulfonic acid was added, and the mixture was heated under reflux for 3 hours while removing the produced water. After cooling, the reaction solution was poured into ice-cooled saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate. The organic layers were combined, the drying agent was removed by filtration and then the solvent was concentrated under a reduced pressure to give 1.38 g of N-(2-(4,5-dihydro-1H-thieno[2,3-g]indol-1-yl)ethyl]acetaamide. From this compound, N-[2-(1H-thieno[2,3-g]indol-1-yl)ethyl]acetamide was obtained in the similar manner as described in Reference Example 60.

Workup

  1. customat 24 to 26° C.
  2. extractionAfter extraction of the reaction mixture with ethyl acetate
  3. washwashed with 2% sodium thiosulfate aqueous solution, water and brine in that order
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customAfter removal of the drying agent
  6. concentrationthe solvent was concentrated under a reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-3989644e7f3f49f48c59d12e4938a41d
Source dataset
uspto-grants-2001_06
Patent number
US06245796B1

Reaction notes

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