Aluminium lithium hydride → HCID 90455723, compound

HRID 2202128Notes

Reaction equation

HRID 2202128 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[N:16][O:17][C:18]=2[C:19](OCC)=[O:20])=[CH:10][CH:9]=1>O1CCCC1>[F:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:15]=[N:16][O:17][C:18]=2[CH2:19][OH:20])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90455740HCID 90455740, compound

Product 1

HCID 90455723HCID 90455723, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-60 °C

Procedure

To a stirred mixture of LiAlH4 (259 mg, 6.82 mmol, 2.01 equiv) in anhydrous tetrahydrofuran (10 mL) maintained under nitrogen at −60° C. was added dropwise a solution of ethyl 4-(4-fluorophenyl)-1,2-oxazole-5-carboxylate (800 mg, 3.40 mmol, 1.00 equiv) in tetrahydrofuran (10 mL). The reaction mixture was stirred at −35° C. for 1 h and then quenched by 2.5 mL of saturated NH4Cl solution. The solid material was removed by filtration. The filtrate was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 10-15% of ethyl acetate in petroleum ether to give 300 mg (46%) of (4-(4-fluorophenyl)isoxazol-5-yl)methanol as a yellow oil. 1H-NMR (300 MHz, CDCl3): δ 8.53 (s, 1H), 7.55-7.50 (m, 2H), 7.20-7.07 (m, 2H), 4.87 (s, 2H) ppm. LCMS (method C, ESI): RT=0.79 min, m/z=194.0 [M+H]+.

Workup

  1. customquenched by 2.5 mL of saturated NH4Cl solution
  2. customThe solid material was removed by filtration
  3. dry with materialThe filtrate was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified on a silica gel column
  6. washeluted with 10-15% of ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-5ae6348f8f0a4381b9d5ff22c9e14335
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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