Pyridine → 3-Octadecyloxycarbonyloxy-1-[6-(triphenylmethoxy)hexyloxyl]-2-methylenepropane

HRID 2166441Notes

Reaction equation

HRID 2166441 reaction equation
[C:1]1([C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][C:17](=[CH2:20])[CH2:18][OH:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[CH2:39]([O:57][C:58](Cl)=[O:59])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56].CCOCC>C(Cl)Cl>[CH2:39]([O:57][C:58]([O:19][CH2:18][C:17](=[CH2:20])[CH2:16][O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][C:7]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:59])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 103922Carbonochloridic acid, octadecyl esterHCID 230396333-[6-(Triphenylmethoxy)hexyloxy]-2-methylenepropan-1-ol

Product 1

HCID 230396403-Octadecyloxycarbonyloxy-1-[6-(triphenylmethoxy)hexyloxyl]-2-methylenepropane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-[6-(triphenylmethoxy)hexyloxy]-2-metylenepropane-1-ol (from Preparation 46) (1.5 g) and pyridine (4.5 ml) in methylene chloride (15 ml) was cooled in an ice/water bath and octadecyloxycarbonyl chloride (1.3 g) was added. After stirring for 10 minutes at 0° C. the temperature was raised to 22° C. for 5 hours. Ether (15 ml) was added, and the mixture was filtered. The filtrate was evaporated to dryness in vacuo, and the residue was purified through a column of silica gel 60 (70-230 mesh, 15 g) eluting with ether/methylene chloride 1:1. Further purification was achieved by chromatography on Waters PrepLC®/System 500A using a prepPAK®-500/SILICA cartridge with ether/methylene chloride/pentane 1:1:3 as eluent.

Workup

  1. temperaturewas cooled in an ice/water bath
  2. temperaturewas raised to 22° C. for 5 hours
  3. filtrationthe mixture was filtered
  4. customThe filtrate was evaporated to dryness in vacuo
  5. customthe residue was purified through a column of silica gel 60 (70-230 mesh, 15 g)
  6. washeluting with ether/methylene chloride 1:1
  7. customFurther purification

Sources & evidence

ORD record
ord-b9b334019e1a4640b0a3ac8ad7ba8dc2
Source dataset
uspto-grants-1990_07
Patent number
US04945098

Reaction notes

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