Aluminium lithium hydride → HCID 86674041, compound

HRID 573960Notes

Reaction equation

HRID 573960 reaction equation
[CH2:1]([O:19][C:20]1[CH:21]=[C:22]([CH:27]=[C:28]([O:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH3:67])[C:29]=1[O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[CH2:23][N:24]=[N+]=[N-])[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][CH2:16][CH2:17][CH3:18].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:50]([O:49][C:28]1[CH:27]=[C:22]([CH:21]=[C:20]([O:19][CH2:1][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][CH2:16][CH2:17][CH3:18])[C:29]=1[O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[CH2:23][NH2:24])[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH3:67]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86674040HCID 86674040, compound

Product 1

HCID 86674041HCID 86674041, compoundYield 105.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, 3,4,5-tris(octadecyloxy)benzyl azide (3.00 g, 3.21 mmol) was dissolved in dehydrating tetrahydrofuran (35 mL) and, under ice-cooling, lithium aluminum hydride (162 mg, 4.30 mmol) was added. The reaction mixture was stirred at room temperature for 2 hr. After completion of the reaction, purified water (2 mL) and 4.0 mol/L aqueous sodium hydroxide solution (2 mL) were added dropwise to the reaction mixture to decompose unreacted lithium aluminum hydride, and the reaction mixture was filtered through celite. The filtrate was concentrated under reduced pressure, acetonitrile was added, and the precipitated solid was collected by filtration and dried under reduced pressure to quantitatively give the title compound (3.09 g) as a white solid.

Workup

  1. temperatureunder ice-cooling
  2. customAfter completion of the reaction
  3. custompurified water (2 mL) and 4.0 mol/L aqueous sodium hydroxide solution (2 mL)
  4. additionwere added dropwise to the reaction mixture
  5. filtrationthe reaction mixture was filtered through celite
  6. concentrationThe filtrate was concentrated under reduced pressure, acetonitrile
  7. additionwas added
  8. filtrationthe precipitated solid was collected by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-54e7d22bbbea4434b94caaa1f186151c
Source dataset
uspto-grants-2015_05
Patent number
US09029528B2

Reaction notes

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