Hydrochloric Acid → Ethyl 7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2,2-dimethyl-7-phenylheptanoate

HRID 1464528

反応式

HRID 1464528 の反応式
C([Li])CCC.CCCCCC.C(NC(C)C)(C)C.[C:19]([O:24][CH2:25][CH3:26])(=[O:23])[CH:20]([CH3:22])[CH3:21].I[CH2:28][CH2:29][CH2:30][CH2:31][CH:32]([C:39]1[C:44]([CH3:45])=[C:43]([O:46][CH3:47])[C:42]([CH3:48])=[C:41]([CH3:49])[C:40]=1[O:50][CH3:51])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl.C(OC(C)C)(C)C.[Cl-].[Na+]>O1CCCC1>[CH3:51][O:50][C:40]1[C:41]([CH3:49])=[C:42]([CH3:48])[C:43]([O:46][CH3:47])=[C:44]([CH3:45])[C:39]=1[CH:32]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:31][CH2:30][CH2:29][CH2:28][C:20]([CH3:22])([CH3:21])[C:19]([O:24][CH2:25][CH3:26])=[O:23]

参加物

9

反応物 7

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 7342Ethyl isobutyrateHCID 7912DiisopropylamineHCID 7914Diisopropyl EtherHCID 190880841-Iodo-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-5-phenylpentaneHCID 178418244HCID 178418244、化合物

生成物 1

HCID 19088026Ethyl 7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2,2-dimethyl-7-phenylheptanoate収率 247.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-12.5 °C

実験手順

A 2.1 ml (3.0×1.1 mmole) portion of n-butyllithium·hexane solution was added dropwise to a solution of 0.50 ml (3.0×1.2 mmole) of diisopropylamine in anhydrous tetrahydrofuran (5 ml) under an atmosphere of argon at -20° C. over the period of 5 minutes, followed by stirring at -20 to -5° C. for 10 minutes. The mixed solution was cooled at -20° C. and a solution of 0.38 g (3.0×1.1 mmole) of ethyl isobutyrate in tetrahydrofuran (4 ml) was added dropwise to it over the period of 5 minutes, followed by stirring at -20° to -5° C. for 20 minutes. A solution of 1.36 g (3.0 mmole) of 1-iodo-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-5-phenylpentane in tetrahydrofuran (14 ml) was added dropwise to the mixed solution over the period of 5 minutes, followed by stirring at -20° to -10° C. for 1.5 hours. After the reaction solution was cooled with ice, the reaction was suspended by adding 1N hydrochloric acid, and isopropyl ether and sodium chloride were added to extract the product. The organic layer was separated out, washed with aqueous saturated sodium chloride solution, dried (magnesium sulfate) and evaporated. The residual solution was chromatographed on a silica gel column to perform purification (elution with hexane/isopropyl ether) to thereby give 1.20 g (91%) of ethyl 7-(2,5-dimethoxy-3,4,6-trimethylphenyl)-2,2-dimethyl-7-phenylheptanoate. Its typical physical properties and nuclear magnetic resonance spectrum data are shown in Table 14.

後処理

  1. temperatureThe mixed solution was cooled at -20° C.
  2. stirringby stirring at -20° to -5° C. for 20 minutes
  3. stirringby stirring at -20° to -10° C. for 1.5 hours
  4. temperatureAfter the reaction solution was cooled with ice
  5. additionwere added
  6. extractionto extract the product
  7. customThe organic layer was separated out
  8. washwashed with aqueous saturated sodium chloride solution
  9. dry with materialdried (magnesium sulfate)
  10. customevaporated
  11. customThe residual solution was chromatographed on a silica gel column
  12. custompurification (elution with hexane/isopropyl ether)

出典と根拠

ORDレコード
ord-743adf5d8fbc401cb62ae0ba583e97ed
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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