Aluminium lithium hydride → HCID 131720506, compound

HRID 863192Notes

Reaction equation

HRID 863192 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C@H:7]([C:15](N(C)OC)=[O:16])[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:5])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([O:3][C:4]([NH:6][C@H:7]([CH:15]=[O:16])[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 131720504HCID 131720504, compound

Product 1

HCID 131720506HCID 131720506, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To 57 mg (200 μmole) (16) was added 1.8 mL of dry THF, and the solution was cooled to 0° C. Then 9.5 mg of lithium aluminum hydride (250 μmole, 1.25 eq H-) was added, and the reaction was monitored by TLC. After 45 min the reaction was quenched with ca. 20 mL ethyl acetate and the solution stirred for 40 min. The organic layer was washed 1× with 5% citric acid and 1× with 5% NaHCO3. The organic layer was dried with Na2SO4, filtered, and the filtrate evaporated. The residue was pumped on high vacuum overnight to give the title compound. NMR (300 MHz, CDCl3): δ 9.52 (s, CHO, 1H), 4.27 (br m, Cha-α, 1H), 4.04 (q, CH3CH2OCO, 2H), 1.80-0.80 (m, cHxCH2, 13H), 1.17 (t, CH3CH2OCO, 3H).

Workup

  1. customAfter 45 min the reaction was quenched with ca. 20 mL ethyl acetate
  2. washThe organic layer was washed 1× with 5% citric acid and 1× with 5% NaHCO3
  3. dry with materialThe organic layer was dried with Na2SO4
  4. filtrationfiltered
  5. customthe filtrate evaporated
  6. customwas pumped on high vacuum overnight

Sources & evidence

ORD record
ord-e92ff6170c144a09a981e9b4bf533cc9
Source dataset
uspto-grants-1998_02
Patent number
US05719296

Reaction notes

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