Tosylmethyl isocyanide → 5,7-dichloro-2,3-dihydro-1H-indene-1-carbonitrile

HRID 1508186Notes

Reaction equation

HRID 1508186 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[C:7](=O)[CH2:6][CH2:5]2.CC1C=CC(S([CH2:23][N+:24]#[C-])(=O)=O)=CC=1.C(O[K])(C)(C)C>COCCOC.CCO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[CH:7]([C:23]#[N:24])[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 161915Tosylmethyl isocyanideHCID 222923465,7-Dichloro-2,3-dihydro-1H-inden-1-oneHCID 178418922HCID 178418922, compound

Product 1

HCID 712392435,7-dichloro-2,3-dihydro-1H-indene-1-carbonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 5,7-dichloro-1-indanone (2.24 mmol) and TosMIC (6.71 mmol) in 25 mL 1,2-dimethoxyethan and 1 mL EtOH was added tBuOK (6.71 mmol) at 5° C. The cooling bath was removed and the reaction mixture was stirred at RT for 1 h. The reaction was quenched with water and extracted with EtOAc (3×). The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by CC using Hept/EtOAc (7/3) gives the desired compound as yellow solid.

Workup

  1. customThe cooling bath was removed
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by CC

Sources & evidence

ORD record
ord-d7d5c937ddd2418288e2a37ed67cdff6
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

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