Aluminium lithium hydride → HCID 71619143, compound

HRID 2276822Notes

Reaction equation

HRID 2276822 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:63])([F:62])[C:9]([O:18][CH2:19][C:20]([CH2:47][O:48][C:49]([C:58]([F:61])([F:60])[F:59])([C:54]([F:57])([F:56])[F:55])[C:50]([F:53])([F:52])[F:51])([CH2:32][O:33][C:34]([C:43]([F:46])([F:45])[F:44])([C:39]([F:42])([F:41])[F:40])[C:35]([F:38])([F:37])[F:36])[CH2:21][O:22][CH2:23][CH2:24][C:25](OC(C)(C)C)=[O:26])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11]>C1COCC1>[F:7][C:8]([F:62])([F:63])[C:9]([O:18][CH2:19][C:20]([CH2:32][O:33][C:34]([C:35]([F:36])([F:37])[F:38])([C:39]([F:40])([F:41])[F:42])[C:43]([F:44])([F:45])[F:46])([CH2:47][O:48][C:49]([C:50]([F:53])([F:52])[F:51])([C:54]([F:55])([F:56])[F:57])[C:58]([F:61])([F:60])[F:59])[CH2:21][O:22][CH2:23][CH2:24][CH2:25][OH:26])([C:10]([F:13])([F:12])[F:11])[C:14]([F:17])([F:16])[F:15]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 71619040HCID 71619040, compound

Product 1

HCID 71619143HCID 71619143, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(—OH version of 19F-27): To a suspension of lithium aluminum hydride (4.1 g, 108 mmol) in THF solution (450 mL) at 0° C. was added dropwise compound 4 (40 g, 43.5 mmol) in THF (100 mL). Afterward, the solution was stirred overnight at room temperature and quenched with dilute HCl carefully, concentrated through rotary evaporation, and subjected to silica gel chromatography using hexane/EtOAc as the eluent to afford alcohol 5 (33.7 g, 39.7 mmol, 91% yield) as a clear oil: 1H NMR (500 MHz, CDCl3) δ 4.02 (s, 6H), 3.69 (t, J=6.0 Hz, 2H), 3.51 (t, J=4.5 Hz, 2H), 3.37 (s, 2H), 1.82-1.77 (m, 2H), 1.47 (s, 9H); 13C NMR (126 MHz, CDCl3) δ 120.4 (q, J=294.7 Hz), 80.1-79.4 (m), 69.3, 66.3, 66.7, 60.4, 46.4, 32.5; 19F NMR (470 MHz, CDCl3) δ—73.40 (s); MS (APCI) m/z 849 (M+H)+; HRMS (ESI) calcd for C20H16F27O5 849.0567 (M+H)+, 866.0832 [M+NH4]+. found 849.0577, 866.0811, respectively.

Workup

  1. customquenched with dilute HCl carefully
  2. concentrationconcentrated through rotary evaporation

Sources & evidence

ORD record
ord-8ba075f657c141cab3dc70e41365929b
Source dataset
uspto-grants-2015_09
Patent number
US09133114B2

Reaction notes

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