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

HRID 863883

반응식

HRID 863883 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

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 yacuo. The residue is partitioned between ethyl acetate and water, the organic phase dried (sodium sulfate) and concentrated in vacuo 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. MS(CI): m/z 227 and 229(MH+ (-TolSH)). Calcd for C19H23ClO2S 1/8H2O: C=63.80, H=6.59, Cl=11.15, S=8.95 Found C=63.68, H=6.44, Cl=10.89, S=8.98

후처리

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

출처 및 근거

ORD 기록
ord-8d28c9c0f6464ee1aeb57ebfa28db2c8
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05561141

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