Sodium hydride → HCID 69051121, compound

HRID 1818095Notes

Reaction equation

HRID 1818095 reaction equation
[C:1]1([CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS([O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][C:41]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)(=O)=O.[H-].[Na+]>CN(C)C=O>[C:42]1([C:41]([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[O:40][CH2:39][CH2:38][O:37][CH2:36][CH2:35][O:34][CH2:33][CH2:32][O:31][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11164646Hexaethylene Glycol Monobenzyl EtherHCID 15297852HCID 15297852, compound

Product 1

HCID 69051121HCID 69051121, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 17-phenylmethyloxy-3,6,9,12,15-pentaoxaheptadecan-1-ol (15) (16.38 g, 43.9 mmol) in dry dimethylformamide (250 ml) was added 8-triphenylmethyloxy-3,6-dioxaoctyl methanesulfonate (13) (28.23 g, 60 mmol, 1.35 eq.) and sodium hydride (4.0 g, 100 mmol, 2.3 eq., 60% w/w in mineral oil). The reaction was left to stir for four days at room temperature after which time it was concentrated in vacuo. The reaction mixture was re-dissolved in diethyl ether (400 ml) and cooled in an ice bath to 0° C. Water was then slowly added until hydrogen was no longer evolved. The organic phase was ten partitioned twice with aq. sat. NaCl with a little NaHCO3 (2×300 ml), dried over anhydrous sodium sulphate and concentrated in vacuo to give a viscous dark brown oil. The product was isolated by N.P.S.G. chromatography, eluting with ethyl acetate only to yield (16) as a yellow oil (24.2 g, 75.0%).

Workup

  1. waitThe reaction was left
  2. concentrationwas concentrated in vacuo
  3. dissolutionThe reaction mixture was re-dissolved in diethyl ether (400 ml)
  4. temperaturecooled in an ice bath to 0° C
  5. additionWater was then slowly added until hydrogen
  6. custompartitioned twice with aq. sat. NaCl with a little NaHCO3 (2×300 ml)
  7. dry with materialdried over anhydrous sodium sulphate
  8. concentrationconcentrated in vacuo
  9. customto give a viscous dark brown oil
  10. customThe product was isolated by N.P.S.G
  11. washchromatography, eluting with ethyl acetate only

Sources & evidence

ORD record
ord-d9c41044e87847d682abe1577c394c58
Source dataset
uspto-grants-2009_10
Patent number
US07598421B2

Reaction notes

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