Iodoethane → HCID 178466915, 화합물

HRID 2172543노트

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HRID 2172543 반응식
[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]

참가 물질

8

반응물 6

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

생성물 1

HCID 178466915HCID 178466915, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9ab4db3b20704cd89e5a8cc9e3147483
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09055743B2

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