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

HRID 1289383노트

반응식

HRID 1289383 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
180 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-7d19e26cf6574bff8faa4e75fcbbce05
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05750213

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