Water → HCID 13655992, compound

HRID 2248381Notes

Reaction equation

HRID 2248381 reaction equation
[C:1]([N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.Cl[C:31]([O:33][CH3:34])=[O:32].O>O1CCCC1.CCCCCC>[C:31]([C:21]1[N:20]([C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:24]=[CH:23][N:22]=1)([O:33][CH3:34])=[O:32]

Participants

7

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 618231DechloroclotrimazoleHCID 178418339Butyllithium

Product 1

HCID 13655992HCID 13655992, compoundYield 21.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of 12.4 g (40 mmol.) of 1-tritylimidazole in 250 mL of tetrahydrofuran, under argon, at 0° C. was added 20 mL (48 mmol.) of a solution of n-butyl-lithium in hexane. After the solution was allowed to warm to ambient temperature, it was stirred for 1 hour and then 3.4 mL (50 mmol.) of methyl chloroformate was added dropwise. The mixture was stirred for 20 hours at 25° C., 100 mL of water was added and then the mixture was concentrated in vacuo. The residue was extracted with ether. After the extracts were dried (MgSO4) and concentrated, the residue was chromatographed on 200 g of silica using 1:3 ethyl acetate: hexane, followed by 1:1 ethyl acetate: hexane, and finally ethyl acetate to give 3.2 g of colorless product.

Workup

  1. stirringThe mixture was stirred for 20 hours at 25° C.
  2. concentrationthe mixture was concentrated in vacuo
  3. extractionThe residue was extracted with ether
  4. dry with materialAfter the extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. customthe residue was chromatographed on 200 g of silica using 1:3 ethyl acetate

Sources & evidence

ORD record
ord-53fc50d0027e47edbbf0ebd395e2251c
Source dataset
uspto-grants-1991_08
Patent number
US05039691

Reaction notes

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