Water → (R)-1-(7-ethoxy-1,4-dihydro-indeno[2,1-c]pyrazol-1-yl)-propan-2-ol

HRID 864071Notes

Reaction equation

HRID 864071 reaction equation
[OH:1][CH:2]=[C:3]1CC2C(=CC(OCC)=CC=2)C1=O.[NH:16]([CH2:18][C@H:19]([OH:21])[CH3:20])[NH2:17].[C:22]1([CH3:32])[CH:27]=[CH:26][C:25](S(O)(=O)=O)=[CH:24][CH:23]=1.O.[C:34]1(C)[CH:39]=CC=C[CH:35]=1>>[CH2:2]([O:1][C:23]1[CH:24]=[CH:25][CH2:26][C:27]2[C:22]=1[CH:32]=[C:35]1[C:34]=2[CH:39]=[N:17][N:16]1[CH2:18][C@H:19]([OH:21])[CH3:20])[CH3:3]

Participants

6

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 28082612(R)-1-hydrazino-2-propanolHCID 701844102-Hydroxymethylene-6-ethoxy-1-indanone

Product 1

HCID 22866137(R)-1-(7-ethoxy-1,4-dihydro-indeno[2,1-c]pyrazol-1-yl)-propan-2-olYield 77%

Procedure

A solution of 0.5 g (2.45 mmol) of 2-hydroxymethylene-6-ethoxy-1-indanone, 0.27 g (2.94 mmol) of (R)-1-hydrazino-2-propanol and 50 mg of p-toluenesulfonic acid in 50 ml of anhydrous toluene was heated on a water separator for 1 hour. After concentration in a vacuum, the reaction mixture was purified by column chromatography on silica gel (ethyl acetate). 0.49 g (77%) of (R)-1-(7-ethoxy-1,4-dihydro-indeno[2,1-c]pyrazol-1-yl )-propan-2-ol was obtained as a yellow solid which was used directly in the next as reaction.

Workup

  1. concentrationAfter concentration in a vacuum
  2. customthe reaction mixture was purified by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-37ada3f61c384d659ac536dd0b9f3dde
Source dataset
uspto-grants-1996_10
Patent number
US05561150

Reaction notes

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