Lithium Hydroxide → 2,2-Bis(4-nitrobenzyl)malonic acid

HRID 921586노트

반응식

HRID 921586 반응식
CC1(C)[O:7][C:6](=[O:8])[C:5]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[C:4](=[O:29])[O:3]1.C1COCC1.[Li+].[OH-]>O>[N+:16]([C:13]1[CH:12]=[CH:11][C:10]([CH2:9][C:5]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)([C:4]([OH:29])=[O:3])[C:6]([OH:8])=[O:7])=[CH:15][CH:14]=1)([O-:18])=[O:17]

참가 물질

5

반응물 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 46194582,2-Dimethyl-5,5-bis(4-nitrobenzyl)-1,3-dioxane-4,6-dione

생성물 1

HCID 229285922,2-Bis(4-nitrobenzyl)malonic acid수율 87.2%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

An adaptation of the procedure described by Tiefenbacher and Rebek (2012) was followed. To a suspension of 5.33 g (12.9 mmol) of 2,2-dimethyl-5,5-di(4-nitrobenzyl)-1,3-dioxane-4,6-dione in 60 mL of a 9:1 mixture of THF to water was added 1.11 g (46.3 mmol) LiOH. This suspension was stirred for ˜17 h. After stirring, 100 mL of water was added to the suspension. The aqueous solution was washed twice with 50 mL of diethyl ether. The aqueous solution was then acidified to pH=1. The product was extracted with ethyl acetate. The ethyl acetate solution was washed once with 100 ml of water and once with 100 mL of brine. The ethyl acetate solution was dried with MgSO4 and the solvent was removed in vacuo to yield 4.21 g (87%) of the desired material. IR, 1HNMR, 13CNMR in addition to TLC were used to confirm identity of the product.

후처리

  1. stirringAfter stirring
  2. washThe aqueous solution was washed twice with 50 mL of diethyl ether
  3. extractionThe product was extracted with ethyl acetate
  4. washThe ethyl acetate solution was washed once with 100 ml of water and once with 100 mL of brine
  5. dry with materialThe ethyl acetate solution was dried with MgSO4
  6. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-3ac3855f421a4ab2badeabd480991837
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09274395B2

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