Acetone → HCID 57679172, compound

HRID 733443Notes

Reaction equation

HRID 733443 reaction equation
CC(C)=O.[O:5]1CCO[CH:6]1[CH2:10][C:11]1([CH2:20][N:21]([CH3:29])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>CCOCC>[CH3:29][N:21]([CH2:20][C:11]1([CH2:10][CH:6]=[O:5])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1)[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:25])[CH3:26]

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 57679159HCID 57679159, compound

Product 1

HCID 57679172HCID 57679172, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

An acetone solution of tert-butyl [1-(1,3-dioxolan-2-ylmethyl)-2,3-dihydro-1H-inden-1-yl]methyl(methyl)carbamate (14.33 g, 41.24 mmole), para-toluene sulfonic acid (1 equivalent) and 50 ml of water were stirred overnight at room temperature. Evaporation of the acetone resulted in an oily slurry. Ether was added and washed with water, followed by NaHCO3 sat. and dried over MgSO4. Evaporation of the ether followed by flash chromatography on silica with 15% EtOAc and hexanes afforded 6.9383 g of tert-butyl methyl{[1-(2-oxoethyl)-2,3-dihydro-1H-inden-1-yl]methyl}carbamate as an oil.

Workup

  1. customEvaporation of the acetone
  2. customresulted in an oily slurry
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customEvaporation of the ether

Sources & evidence

ORD record
ord-ee24a11238c54a0c831b1f6002ebbb60
Source dataset
uspto-grants-2009_09
Patent number
US07589204B2

Reaction notes

Loading…