p-Toluenesulfonic acid → HCID 19935702, compound

HRID 37705

Reaction equation

HRID 37705 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]3[NH:15][CH:16]=[C:17]([CH2:18][CH2:19][OH:20])[C:11]=3[CH:10]=2)=[CH:3][CH:2]=1.[CH2:21]([C:23]([CH2:25][CH3:26])=O)[CH3:22].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:21]([C:23]1([CH2:25][CH3:26])[C:16]2[NH:15][C:12]3[C:11]([C:17]=2[CH2:18][CH2:19][O:20]1)=[CH:10][C:9]([O:8][CH2:7][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1)=[CH:14][CH:13]=3)[CH3:22]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7288Ethyl ketoneHCID 7448495-Benzyloxy-3-(2-hydroxyethyl)indole

Product 1

HCID 19935702HCID 19935702, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture consisting of 5-benzyloxytryptophol (7.0 g, 0.0262 mol), diethyl ketone (10 mL), benzene (400 mL) and p-toluene sulfonic acid is refluxed for 3.5 hours using a Dean-Stark tap to remove the water. The reaction mixture is cooled to room temperature, washed with 5% sodium bicarbonate, water (200 mL), brine (200 mL), dried (MgSO4), filtered and concentrated to give 9.9 g of crude product. The crude product is flash chromatographed on silica gel using 15% ethyl acetate/hexane as an eluent to afford 6.5 g of pure title compound.

Workup

  1. temperatureis refluxed for 3.5 hours
  2. customto remove the water
  3. washwashed with 5% sodium bicarbonate, water (200 mL), brine (200 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give 9.9 g of crude product
  8. customchromatographed on silica gel using 15% ethyl acetate/hexane as an eluent

Sources & evidence

ORD record
ord-a09d1d9c3a1d4cbca6ef532f7dd1bb33
Source dataset
uspto-grants-1995_05
Patent number
US05420289

Linked notes

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