1,2-di-O-(n-hexadecyl)-3-allyl-glycerol → 1,2-Di-O-(n-hexadecyl)-3-O-formylmethyl-glycerol

HRID 2058391Notes

Reaction equation

HRID 2058391 reaction equation
[CH2:1]([O:17][CH2:18][CH:19]([CH2:37][O:38][CH2:39][CH:40]=C)[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].I([O-])(=O)(=O)=[O:43].[Na+]>O1CCCC1.O.O.[Os](=O)(=O)(=O)=O>[CH2:1]([O:17][CH2:18][CH:19]([CH2:37][O:38][CH2:39][CH:40]=[O:43])[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 2

HCID 234661031,2-di-O-(n-hexadecyl)-3-allyl-glycerolHCID 23667635Sodium periodate

Product 1

HCID 887574871,2-Di-O-(n-hexadecyl)-3-O-formylmethyl-glycerolYield 57%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Osmium tetroxide (90 mg., 0.354 mmoles) was added to a solution of 1,2-di-O-(n-hexadecyl)-3-O-allyl-glycerol (4.5 g., 7.75 mmoles) in tetrahydrofuran:water (3:1, 120 ml.), and the resulting solution stirred for 5 minutes at room temperature. Sodium periodate (9 g., 42 mmoles) was then added and the reaction solution stirred for 16 hours at room temperature under nitrogen. The reaction solution was then diluted with water (150 ml.) and extracted with ether (2×150 ml.). The combined ether extract was washed with water (150 ml.), dried (MgSO4) and evaporated in vacuo to an oil, which was purified by silica gel chromatography (elution with benzene:ethyl acetate) [2.6 g., 57% yield, waxy solid, ir (CHCl3) 1735 cm-1, n.m.r. (CDCl3) δ9.38 (t, J=1 Hz, 1, --OCH2CHO) and 4.07 (d, J=1 Hz, 2, --OCH2CHO)].

Workup

  1. stirringthe reaction solution stirred for 16 hours at room temperature under nitrogen
  2. extractionextracted with ether (2×150 ml.)
  3. extractionThe combined ether extract
  4. washwas washed with water (150 ml.)
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo to an oil, which
  7. customwas purified by silica gel chromatography (elution with benzene:ethyl acetate) [2.6 g., 57% yield, waxy solid, ir (CHCl3) 1735 cm-1, n.m.r. (CDCl3) δ9.38 (t, J=1 Hz, 1, --OCH2CHO) and 4.07 (d, J=1 Hz, 2, --OCH2CHO)]

Sources & evidence

ORD record
ord-6f75c03694e444fc93ea0e441375b786
Source dataset
uspto-grants-1980_07
Patent number
US04215146

Reaction notes

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