Tetrahydrofuran → HCID 70119328, 화합물

HRID 1458494노트

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HRID 1458494 반응식
O[C@H:2]1[C@H:7]([OH:8])[O:6][CH2:5][CH2:4][O:3]1.[H-].[Na+].[O:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.S(C1C=CC(C)=CC=1)([O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][O:42][C:43](=[O:46])[CH:44]=[CH2:45])=[CH:29][N:28]=2)=[CH:23][CH:22]=1)(=O)=O>O>[C:43]([O:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][O:33][C:30]1[CH:29]=[N:28][C:27]([C:24]2[CH:25]=[CH:26][C:21]([CH2:20][O:19][C@H:2]3[C@H:7]([O:8][CH2:20][C:21]4[CH:26]=[CH:25][C:24]([C:27]5[N:32]=[CH:31][C:30]([O:11][CH2:15][CH2:14][CH2:13][CH2:12][CH2:38][CH2:39][CH2:40][CH2:41][O:42][C:43](=[O:46])[CH:44]=[CH2:45])=[CH:29][N:28]=5)=[CH:23][CH:22]=4)[O:6][CH2:5][CH2:4][O:3]3)=[CH:22][CH:23]=2)=[N:32][CH:31]=1)(=[O:46])[CH:44]=[CH2:45]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 155105667907-42-0HCID 131720986HCID 131720986, 화합물

생성물 1

HCID 70119328HCID 70119328, 화합물

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of 0.2 g of trans-2,3-dihydroxy-1,4-dioxane, 0.5 g of sodium hydride and 50 ml of tetrahydrofuran is stirred for 7 hours. 1.1 g of 4-(5-[8-acryloyloxyoctyloxy]pyrimidin-2-yl)benzyl tosylate are added and the mixture is stirred at room temperature overnight, poured into 100 ml of water and then extracted three times with 50 ml of diethyl ether each time. The organic phases are combined, washed twice with 100 ml of water each time, dried over magnesium sulphate, filtered and the filtrate is concentrated. Chromatographic purification of the residue on silica gel with cyclohexane/ethyl acetate (vol. 8:2) and two-fold recrystallization from a cyclohexane/ethyl acetate mixture (vol. 8:2) of the fractions which are pure according to thin-layer chromatography gives 1.1 g of trans-2,3-bis[4-(5-[8-acryloyloxyoctyloxy]pyrimidin-2-yl)benzyloxy]-1,4-dioxane.

후처리

  1. extractionextracted three times with 50 ml of diethyl ether each time
  2. washwashed twice with 100 ml of water each time
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated
  6. customChromatographic purification of the residue on silica gel
  7. customwith cyclohexane/ethyl acetate (vol. 8:2) and two-fold recrystallization from a cyclohexane/ethyl acetate mixture (vol. 8:2) of the fractions which

출처 및 근거

ORD 기록
ord-6277b1d340424fe79a991e5a1194fbdd
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05851424

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