Aluminium lithium hydride → HCID 178448134, compound

HRID 1613200Notes

Reaction equation

HRID 1613200 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:14][CH2:13][C@H:12](/[CH:15]=[C:16](\[CH3:22])/[C:17](OCC)=[O:18])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Si:1]([O:8][C@@H:9]1[CH2:10][CH2:11][C@H:12](/[CH:15]=[C:16](\[CH3:22])/[CH2:17][OH:18])[CH2:13][CH2:14]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178471462HCID 178471462, compound

Product 1

HCID 178448134HCID 178448134, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 300 mg (0.95 mmol) of enoate (19) in 2.0 mL of anhydrous tetrahydrofuran at 25° C. was added 18 mg (0.43 mmol) of lithium aluminum hydride and the resulting mixture was allowed to stir for 30 min. The reaction was quenched by the slow addition of saturated Rochelle's salt and diluted with ethyl acetate. The layers were separated and the aqueous layer was extracted with two portions of ethyl acetate. The combined organic extracts were washed with water and brine and then dried over MgSO4. Evaporation and flash chromatography (elution with 1:10 ethyl acetatehexane) gave 220 mg of the allyic alcohol (20). 1H NMR (300 MHz, CDCl3) δ 5.34 (d), 3.96 (d), 3.85 (m), 2.26-2.18 (m), 1.64 (d), 1.61-1.34 (m), 1.82 (s), 0.0 (s).

Workup

  1. customThe reaction was quenched by the slow addition of saturated Rochelle's salt
  2. additiondiluted with ethyl acetate
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with two portions of ethyl acetate
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over MgSO4
  7. customEvaporation and flash chromatography (elution with 1:10 ethyl acetatehexane)

Sources & evidence

ORD record
ord-b5b501c0fea340988879b94243f07754
Source dataset
uspto-grants-1993_03
Patent number
US05192773

Reaction notes

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