Aluminium lithium hydride → 1,3-Dioleyloxy-2-propylamine

HRID 724765Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:25][CH2:26][CH:27]([N:48]=[N+]=[N-])[CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]/[CH:38]=[CH:39]\[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>O1CCCC1>[CH2:7]([O:25][CH2:26][CH:27]([NH2:48])[CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]/[CH:38]=[CH:39]\[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

Conditions

Temperature: 0 °C

Procedure

In 3 ml of tetrahydrofuran was suspended 8 mg (0.2 mmol) of lithium aluminum hydride. While this suspension was maintained under ice-cooling, 125 mg (0.2 mmol) of 1,3-dioleyloxy-2-propyl azide was added dropwise and the mixture was stirred at 0° C. for 2 hours. The reaction mixture was then poured in ice-water and extracted with ether. The extract was washed with water, dried, and concentrated. The residue was subjected to column chromatography (silica gel/methylene chloride-methanol) to provide 104 mg (89%) of the title compound as colorless oil.

Workup

temperatureWhile this suspension was maintained under ice-
temperaturecooling
extractionextracted with ether
washThe extract was washed with water
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-1653c5ce626d4cafaa3c6add3b44ba1e
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05705188

Reaction notes

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