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Ethylene Glycol → Methyl 8-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-octanoate

HRID 1779232
ノート
印刷プレビュー

反応式

HRID 1779232 の反応式
[O:1]=[C:2]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11].[CH2:24](O)[CH2:25][OH:26].C([O-])([O-])OC>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:18]1([CH2:17][CH2:16][CH2:15][CH2:14][C:2]2([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[O:26][CH2:25][CH2:24][O:1]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 174Ethylene GlycolHCID 53629101MethylorthoformateHCID 90060223HCID 90060223、化合物

生成物 1

HCID 90060217Methyl 8-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-octanoate収率 92%

試薬・触媒・溶媒 2

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 1140
Toluene
溶媒

実験手順

Methyl 9-oxo-13-phenyl-tridecanoate (1.8 g, 5.65 mmol) was dissolved in toluene (5.0 mL), and ethylene glycol (0.935 mL, 16.8 mmol), methyl orthoformate (1.85 mL, 16.8 mmol), and p-toluenesulfonic acid monohydrate (53.0 mg, 0.279 mmol) were then added in order at room temperature. The mixture was stirred for 40 minutes, and then quenched with a saturated aqueous solution (30 mL) of sodium bicarbonate, and 10% methanol/ethyl acetate (100 mL) was then added. The mixture was separated. The organic layer was washed with a mixture of water (10 mL) and a saturated aqueous solution (30 mL) of sodium chloride, dried over anhydrous sodium sulfate, and filtered. The solvent was then distilled off under reduced pressure. The residue was purified on Biotage (silica gel, n-hexane/ethyl acetate) to obtain 1.88 g (5.19 mmol, yield 92%) of methyl 8-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-octanoate.

後処理

  1. customquenched with a saturated aqueous solution (30 mL) of sodium bicarbonate, and 10% methanol/ethyl acetate (100 mL)
  2. additionwas then added
  3. customThe mixture was separated
  4. washThe organic layer was washed with a mixture of water (10 mL)
  5. dry with materiala saturated aqueous solution (30 mL) of sodium chloride, dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. distillationThe solvent was then distilled off under reduced pressure
  8. customThe residue was purified on Biotage (silica gel, n-hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-4654297c0fc54958933b967b67d52830
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09266853B2

反応ノート

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