Tetrahydrofuran → HCID 70119328, compound

HRID 1458494Notes

Reaction equation

HRID 1458494 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

HCID 70119328HCID 70119328, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6277b1d340424fe79a991e5a1194fbdd
Source dataset
uspto-grants-1998_12
Patent number
US05851424

Reaction notes

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