1,10-Phenanthroline → 4-[4-Chloro-1-[(4-methylphenyl)thio]butyl]-1,2-dimethoxybenzene

HRID 1684369

反応式

HRID 1684369 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[CH:5][C:4]=1[O:18][CH3:19].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C([Li])CCC.CCCCCC.Br[CH2:46][CH2:47][CH2:48][Cl:49]>O1CCCC1.C(OCC)(=O)C>[Cl:49][CH2:48][CH2:47][CH2:46][CH:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([O:18][CH3:19])[CH:5]=1)[S:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=1

参加物

7

反応物 4

HCID 13181,10-PhenanthrolineHCID 80061-Bromo-3-chloropropaneHCID 105164711,2-Dimethoxy-4-[[(4-methylphenyl)thio]methyl]benzeneHCID 178418244HCID 178418244、化合物

生成物 1

HCID 108317364-[4-Chloro-1-[(4-methylphenyl)thio]butyl]-1,2-dimethoxybenzene

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of 13.72 g of 1,2-dimethoxy-4-[[(4-methylphenyl)thio]methyl]benzene and a crystal of phenanthroline in 250 mL of tetrahydrofuran (dried over 3A sieves), under nitrogen at -78° C., is added 21.0 mL of 2.5M n-butyl lithium/hexane via a syringe. After 10 minutes, the brown solution is warmed to 0° C. for 1 hour, then it is recooled to -78° C. and 8.02 mL of 1-bromo-3-chloropropane is added via syringe. The reaction is permitted to warm to room temperature overnight. To the now light yellow reaction mixture is added 10 mL of ethyl acetate and the resulting solution concentrated in vacuo. The residue is partitioned between ethyl acetate and water, the organic phase dried (sodium sulfate) and concentrated in yacuo to a yellow oil. Purification by chromatography on silica gel with gradient elution progressing from hexane to chloroform to methyl alcohol, repeated three times, affords 16.47 g of the desired product as a yellow oil.

後処理

  1. customis recooled to -78° C.
  2. temperatureto warm to room temperature overnight
  3. concentrationthe resulting solution concentrated in vacuo
  4. customThe residue is partitioned between ethyl acetate and water
  5. dry with materialthe organic phase dried (sodium sulfate)
  6. concentrationconcentrated in yacuo to a yellow oil
  7. customPurification by chromatography on silica gel with gradient elution progressing from hexane to chloroform to methyl alcohol

出典と根拠

ORDレコード
ord-8fbdda7b0f364c09b351f7e30cd22ed5
出典データセット
uspto-grants-1997_06
特許番号
US05639887

関連ノート

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