Phosphoric Acid → 7-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-7-phenylheptane

HRID 1646818

반응식

HRID 1646818 반응식
C([Li])CCC.[CH2:6]([C:13]1[C:18]([CH3:19])=[C:17]([O:20][CH3:21])[C:16]([CH3:22])=[C:15]([CH3:23])[C:14]=1[O:24][CH3:25])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CC(C)(N)C(C)(C)N.[CH2:34](Br)[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].P(=O)(O)(O)O>O1CCCC1.CCCCCC>[CH3:25][O:24][C:14]1[C:15]([CH3:23])=[C:16]([CH3:22])[C:17]([O:20][CH3:21])=[C:18]([CH3:19])[C:13]=1[CH:6]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

참가 물질

8

반응물 5

HCID 1004Phosphoric AcidHCID 81011-BromohexaneHCID 1233902,3-Butanediamione, 2,3-dimethyl-HCID 190880201-Benzyl-2,5-dimethoxy-3,4,6-trimethylbenzeneHCID 178418339Butyllithium

생성물 1

HCID 190880827-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-7-phenylheptane수율 77.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

A 3.1 ml (5.0 mmole) portion of n-butyllithium.hexane solution was added dropwise to 1.35 g (5.0 mmole) of 1-benzyl-2,5-dimethoxy-3,4,6-trimethylbenzene and 0.83 ml (5×1.1 mmole) of 1,1,2,2-tetramethylethylenediamine dissolved in anhydrous tetrahydrofuran (15 ml), under an atmosphere of argon at 50° C. over the period of 5 miniutes, followed by stirring at 50° to 55° C. for 25 minutes. Then, a solution of 0.83 g (5.0 mmole) of n-hexyl bromide in tetrahydrofuran (5 ml) was added dropwise to the mixed solution over the period of 5 minutes, followed by stirring at 50° C. for further 10 minutes. The reaction solution was cooled with ice and made acid by adding a 10% aqueous phosphoric acid solution, and the product was extracted with isopropyl ether. The organic layer was separated out, washed with aqueous sodium chloride solution, dried (magnesium sulfate) and evaporated. The residual solution was chromatographed on a silica gel column to effect purification (elution with hexane/isopropyl ether) to thereby give 1.37 g (77%) of 7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-7-phenylheptane. Its typical physical properties and nuclear magnetic resonance specrum data are shown in Table 14.

후처리

  1. stirringby stirring at 50° C. for further 10 minutes
  2. temperatureThe reaction solution was cooled with ice
  3. extractionthe product was extracted with isopropyl ether
  4. customThe organic layer was separated out
  5. washwashed with aqueous sodium chloride solution
  6. dry with materialdried (magnesium sulfate)
  7. customevaporated
  8. customThe residual solution was chromatographed on a silica gel column to effect purification (elution with hexane/isopropyl ether)

출처 및 근거

ORD 기록
ord-b0f07b3ee53f4fe5b8a5864654260314
출처 데이터셋
uspto-grants-1993_01
특허 번호
US05180742

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