Aluminium lithium hydride → HCID 59776372, compound

HRID 1008765Notes

Reaction equation

HRID 1008765 reaction equation
[CH3:1][C:2]([CH3:18])([CH2:8][C:9]#[C:10][CH2:11][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[C:3](OCC)=[O:4].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][C:2]([CH3:18])([CH2:8][C:9]#[C:10][CH2:11][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[CH2:3][OH:4]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59776349HCID 59776349, compound

Product 1

HCID 59776372HCID 59776372, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 2,2-dimethyl-6-morpholin-4-ylhex-4-ynoate (380 mg; 1.50 mmol) in THF (5 mL) at 0° C. was added LiAlH4 (2.25 mL; solution 1.00 M in THF; 2.25 mmol). The mixture was stirred at 0° C. for 1 h and quenched with water (80 μL), 80 μL NaOH 15% (80 μL) and water (3×80 μL). The suspension thus obtained was then filtrated through a celite pad and rinsed several times with EtOAc. The filtrate was concentrated under reduced pressure to give 302 mg of the title compound as an orange oil (307 mg, 97% yield). GC/MS, m/z: 211, Rt: 4.13 min.

Workup

  1. customquenched with water (80 μL), 80 μL NaOH 15% (80 μL) and water (3×80 μL)
  2. customThe suspension thus obtained
  3. filtrationwas then filtrated through a celite pad
  4. washrinsed several times with EtOAc
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-18551aa9e87b4e86a6858ea5f4f01096
Source dataset
uspto-grants-2011_07
Patent number
US07973039B2

Reaction notes

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