Iodoethane → HCID 178466915、化合物

HRID 2172543ノート

反応式

HRID 2172543 の反応式
[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]

参加物

8

反応物 6

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

生成物 1

HCID 178466915HCID 178466915、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9ab4db3b20704cd89e5a8cc9e3147483
出典データセット
uspto-grants-2015_06
特許番号
US09055743B2

反応ノート

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