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

HRID 1464522

反応式

HRID 1464522 の反応式
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]

参加物

8

反応物 5

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

生成物 1

HCID 190880827-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-7-phenylheptane収率 77%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

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 minutes, followed by stirring at 50° to 55° C. for 25 minutes. Then, a solution of 0.83 (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.

後処理

  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)

出典と根拠

ORDレコード
ord-be66aef433ea4838aa4ef1014b7dc05c
出典データセット
uspto-grants-1994_04
特許番号
US05304658

関連ノート

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