Aluminium lithium hydride → HCID 135452396, compound

HRID 551832Notes

Reaction equation

HRID 551832 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]3[NH:16][C:15]([C:17]([C:54]4[C:59]([CH3:60])=[CH:58][C:57]([CH3:61])=[CH:56][C:55]=4[CH3:62])=[C:18]4[N:53]=[C:21]([C:22]([C:43]5[CH:48]=[CH:47][C:46]([C:49](OC)=[O:50])=[CH:45][CH:44]=5)=[C:23]5[NH:42][C:26](=[C:27]([C:33]6[C:38]([CH3:39])=[CH:37][C:36]([CH3:40])=[CH:35][C:34]=6[CH3:41])[C:28]6[CH:29]=[CH:30][C:31]=2[N:32]=6)[CH:25]=[CH:24]5)[CH:20]=[CH:19]4)=[CH:14][CH:13]=3)=[CH:7][CH:6]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:2][CH2:3][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]3[NH:16][C:15]([C:17]([C:54]4[C:59]([CH3:60])=[CH:58][C:57]([CH3:61])=[CH:56][C:55]=4[CH3:62])=[C:18]4[N:53]=[C:21]([C:22]([C:43]5[CH:48]=[CH:47][C:46]([CH2:49][OH:50])=[CH:45][CH:44]=5)=[C:23]5[NH:42][C:26](=[C:27]([C:33]6[C:34]([CH3:41])=[CH:35][C:36]([CH3:40])=[CH:37][C:38]=6[CH3:39])[C:28]6[CH:29]=[CH:30][C:31]=2[N:32]=6)[CH:25]=[CH:24]5)[CH:20]=[CH:19]4)=[CH:14][CH:13]=3)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 135428069HCID 135428069, compound

Product 1

HCID 135452396HCID 135452396, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 14 (407 mg, 0.500 mmol) in anhydrous THF (50 mL) was treated with LiAlH4 (76 mg, 2.0 mmol). The reaction mixture was stirred at room temperature. After 15 min, the reaction was quenched with methanol and concentrated. The dark residue was suspended in CHCl3 and poured on to a pad of alumina. The alumina pad was eluted with CHCl3/methanol (4:1) until the eluant was colorless. The solvent was evaporated under vacuum. Chromatography [silica, CHCl3/methanol (4:1)] afforded a purple solid (340 mg, 89%): 1H NMR δ −2.63 (s, 2H), 1.84 (s, 12H), 2.63 (s, 6H), 5.07 (s, 4H), 7.28 (s, 4H), 7.75 (d, J=8.0 Hz, 4H), 8.22 (d, J=8.0 Hz, 4H), 8.69 (d, J=4.8 Hz, 4H), 8.80 (d, J=4.4 Hz, 4H); LD-MS obsd 758.54, calcd 758.3621 (C52H46N4O2); λabs 419, 515, 549, 593, 647 nm.

Workup

  1. customthe reaction was quenched with methanol
  2. concentrationconcentrated
  3. additionpoured on to a pad of alumina
  4. washThe alumina pad was eluted with CHCl3/methanol (4:1) until the eluant
  5. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-7fef2f8c2ced4879a01364ec56ec91bb
Source dataset
uspto-grants-2011_05
Patent number
US07947828B2

Reaction notes

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