Iodoethane → HCID 178466915, compound

HRID 2172543Notes

Reaction equation

HRID 2172543 reaction equation
[CH2:1]([O:3][C:4]1[CH2:9][CH2:8][CH2:7][C:6](=[N:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[CH:5]=1)[CH3:2].CC1C=CC(NC2CCC[C:28](=[O:32])C=2)=CC=1.C(I)C.C([N-]C(C)C)(C)C.[Li+].C(OCC)=O.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:3][C:4]1[CH2:9][CH2:8]/[C:7](=[CH:28]/[OH:32])/[C:6](=[N:10][C:11]2[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[CH:5]=1)[CH3:2]

Participants

8

Reactant 6

HCID 6340IodoethaneHCID 8025Ethyl formateHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 27486243-[(4-Methylphenyl)amino]-2-cyclohexen-1-oneHCID 67811546HCID 67811546, compound

Product 1

HCID 178466915HCID 178466915, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.80 g (12.2 mmol) of N-(3-ethoxycyclohex-2-en-1-ylidene)-4-methylaniline (prepared from 3-[(4-methylphenyl)amino]cyclohex-2-en-1-one and ethyl iodide analogously to J. Org. Chem. 1984, 49, 3314) are dissolved in 40 ml of anhydrous tetrahydrofuran and, at −78° C., 7.94 ml of lithium diisopropylamide solution (2 M in tetrahydrofuran, heptane, ethylbenzene, 15.9 mmol) are added and the mixture is stirred for 30 min. At −78° C., 932 mg (12.2 mmol) of ethyl formate, dissolved in 10 ml of tetrahydrofuran, are added. After 1 h of stirring at −78° C., saturated aqueous ammonium chloride solution is added, the mixture is extracted with ethyl acetate and the organic phase is washed with saturated aqueous sodium chloride solution and dried over sodium sulphate. Purification of the residue by recrystallization (cyclohexane/ethyl acetate) gives 455 mg of (Z)-{4-ethoxy-2-[(4-methylphenyl)imino]cyclohex-3-en-1-ylidene}methanol.

Workup

  1. additionare added
  2. stirringAfter 1 h of stirring at −78° C.
  3. extractionthe mixture is extracted with ethyl acetate
  4. washthe organic phase is washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. customPurification of the residue
  7. customby recrystallization (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-9ab4db3b20704cd89e5a8cc9e3147483
Source dataset
uspto-grants-2015_06
Patent number
US09055743B2

Reaction notes

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