Aluminium lithium hydride → HCID 86701294, compound

HRID 2282996Notes

Reaction equation

HRID 2282996 reaction equation
[CH3:1][C@@H:2]1[O:6][C:5](=[O:7])[C@H:4]([O:8][CH2:9][C:10]([CH3:12])=[CH2:11])[C@H:3]1[O:13][CH2:14][C:15]([CH3:17])=[CH2:16].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:12][C:10](=[CH2:11])[CH2:9][O:8][C@H:4]([C@@H:3]([O:13][CH2:14][C:15]([CH3:17])=[CH2:16])[C@@H:2]([OH:6])[CH3:1])[CH2:5][OH:7]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86701293HCID 86701293, compound

Product 1

HCID 86701294HCID 86701294, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (3R,4S,5S)-5-methyl-3,4-bis(2-methylallyloxy)dihydrofuran-2(3H)-one (1 g, 4.16 mmol) in THF (10 mL) at 0° C. was added 1.0 M LAH (9.57 mL, 9.57 mmol) in THF over 15 min. The mixture was warmed to room temperature and stirred for 2 h, then carefully added dropwise to an ice cold saturated aqueous ammonium chloride (NH4Cl) solution (100 mL). The phases were separated and the aqueous layer was extracted with DCM. The combined organic layers were dried over sodium sulfate (Na2SO4), filtered, and the filtrate was concentrated. Purification by flash chromatography (SiO2) afforded the title compound as a colorless oil (920 mg, 90%): 1H NMR (400 MHz, CDCl3) δ 4.99 (d, J=7.8 Hz, 2H), 4.91 (d, J=8.9 Hz, 2H), 4.09-3.92 (m, 5H), 3.93-3.83 (m, 1H), 3.82-3.73 (m, 1H), 3.70 (q, J=4.7 Hz, 1H), 3.39 (dd, J=6.0, 5.0 Hz, 1H), 3.14 (s, 1H), 2.46 (s, 1H), 1.77 (s, 3H), 1.76 (s, 3H), 1.26 (d, J=6.3 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 141.95, 141.75, 112.99, 112.79, 81.57, 79.41, 75.52, 74.57, 67.60, 61.33, 19.67, 19.63, 19.61.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with DCM
  3. dry with materialThe combined organic layers were dried over sodium sulfate (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customPurification by flash chromatography (SiO2)

Sources & evidence

ORD record
ord-86991bc712ec45af9a54426209324edf
Source dataset
uspto-grants-2015_09
Patent number
US09144239B2

Reaction notes

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