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Water → Methyl 6-(4-methoxycarbonylbenzyl)-8-(2-methoxyphenyl)-7-octenoate

HRID 2243299
ノート
印刷プレビュー

反応式

HRID 2243299 の反応式
[Br-].[CH3:2][O:3][C:4]1[CH:29]=[CH:28][CH:27]=[CH:26][C:5]=1[CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:30]([CH:32]([CH2:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]([O:50][CH3:51])=[O:49])=[CH:44][CH:43]=1)[CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=O.O>C1COCC1>[CH3:51][O:50][C:48]([C:45]1[CH:46]=[CH:47][C:42]([CH2:41][CH:32]([CH:30]=[CH:6][C:5]2[CH:26]=[CH:27][CH:28]=[CH:29][C:4]=2[O:3][CH3:2])[CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])=[CH:43][CH:44]=1)=[O:49]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 962WaterHCID 11255212Methyl 6-formyl-7-(4-methoxycarbonylphenyl)heptanoateHCID 11294197Phosphonium, [(2-methoxyphenyl)methyl]triphenyl-, bromide

生成物 1

HCID 68707125Methyl 6-(4-methoxycarbonylbenzyl)-8-(2-methoxyphenyl)-7-octenoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

At 0° C., 77.4 mg (0.17 mmol) of 2-methoxybenzyltriphenylphosphonium bromide from Ex. IVj are suspended under argon in 20 ml of THF, and 0.115 ml of buthyl-lithium (0.18 mmol, 1.6 M solution in hexane) are added. The deep-orange solution is stirred at 0° C. for 30 min. At this temperature, a solution of 51.2 mg (0.17 mmol) of methyl 6-formyl-7-(4-methoxycarbonylphenyl)heptanoate (synthesis analogously to EP-A-0 341 551, p. 32, Ex. 44) in 15 ml of THF is added dropwise. The mixture is stirred at 0° C. for 30 min. At 0° C., water is added and the mixture is warmed to room temperature and extracted with ethyl acetate. The organic phase is washed with sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. For purification, the substance is chromatographed on silica gel 60 (particle size 0.040-0.063 mm) using cyclohexane/ethyl acetate 9:1 to 1:1 as mobile phase.

後処理

  1. customAt 0° C.
  2. stirringThe mixture is stirred at 0° C. for 30 min
  3. temperaturethe mixture is warmed to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed with sodium chloride solution
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customFor purification
  9. customthe substance is chromatographed on silica gel 60 (particle size 0.040-0.063 mm)

出典と根拠

ORDレコード
ord-55972a5603f14e849eee434b786a63f3
出典データセット
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07674825B2

反応ノート

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