Dimethyl Sulfoxide → Ethyl 2,2-bis(6-benzyloxyhexyl)acetate

HRID 1289383ノート

反応式

HRID 1289383 の反応式
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(C(OCC)=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Li+].CS(C)=O>O>[CH2:33]([O:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 433294Lithium ChlorideHCID 18920850Diethyl 2,2-bis(6-benzyloxyhexyl)malonate

生成物 1

HCID 18920832Ethyl 2,2-bis(6-benzyloxyhexyl)acetate収率 73.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
180 °C

実験手順

First, 14.8 g of diethyl 2,2-bis(6-benzyloxyhexyl)malonate, 0.5 g of water, 2.3 g of lithium chloride, and 50 ml of dimethyl sulfoxide were placed in a 100 ml flask. Then, the mixture was stirred at 180° C. for 12 hours. The reaction mixture was poured into water, and an organic layer was extracted with methylene chloride. The methylene chloride layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1) to obtain 9.4 g of ethyl 2,2-bis(6-benzyloxyhexyl)acetate (Y: 72.9%). The compound thus obtained had a purity of 97.9% by GC.

後処理

  1. extractionan organic layer was extracted with methylene chloride
  2. washThe methylene chloride layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThereafter, the solvent was distilled away
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1)

出典と根拠

ORDレコード
ord-7d19e26cf6574bff8faa4e75fcbbce05
出典データセット
uspto-grants-1998_05
特許番号
US05750213

反応ノート

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