Sodium hydride → 1-(tert-Butyldimethylsilyloxymethyl)-4-(13-allyloxy-2,5,8,11-tetraoxa-tridecyl)-benzene

HRID 1714714Notes

Reaction equation

HRID 1714714 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][OH:16])[CH:2]=[CH2:3].[H-].[Na+].[Si:19]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34]I)=[CH:30][CH:29]=1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>C1COCC1>[Si:19]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][O:16][CH2:15][CH2:14][O:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH2:1][CH:2]=[CH2:3])=[CH:30][CH:29]=1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 101252143,6,9,12-Tetraoxapentadec-14-en-1-olHCID 107373351-[(tert-Butyldimethylsilyl)oxymethyl]-4-iodomethylbenzene

Product 1

HCID 686386381-(tert-Butyldimethylsilyloxymethyl)-4-(13-allyloxy-2,5,8,11-tetraoxa-tridecyl)-benzeneYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 11-allyloxy-3,6,9-trioxaundecanol (83, 2.33 g, 9.94 mmol) in dry THF (40 mL), sodium hydride (0.95 g, 39.8 mmol) is added in several portions under an argon atmosphere. The mixture is stirred for 30 min. A solution of the iodo derivative 45 (3.0 g, 8.28 mmol) in dry THF (10 mL) is added dropwise, and the mixture stirred for 15 h. The reaction is quenched by adding 2 mL of water, and 70% of the amount of THF is evaporated in vacuo. To dilute the mixture, 70 mL of water are added, and the solution extracted with 5 times 50 mL ethyl acetate. The combined organic extracts are dried over MgSO4 and concentrated in vacuo. The yellow oil obtained is purified by flash column chromatography (gradient petrol ether/ethyl acetate 10:1 to 5:1) to give the title product 84 as a pale yellow oil (1.96 g, 4.2 mmol, 51%).

Workup

  1. stirringthe mixture stirred for 15 h
  2. customThe reaction is quenched
  3. additionby adding 2 mL of water, and 70% of the amount of THF
  4. customis evaporated in vacuo
  5. additionTo dilute the mixture, 70 mL of water
  6. additionare added
  7. extractionthe solution extracted with 5 times 50 mL ethyl acetate
  8. dry with materialThe combined organic extracts are dried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe yellow oil obtained
  11. customis purified by flash column chromatography (gradient petrol ether/ethyl acetate 10:1 to 5:1)

Sources & evidence

ORD record
ord-05c0fca5058b4520a8617efc7f70a631
Source dataset
uspto-grants-2010_09
Patent number
US07799524B2

Reaction notes

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