Sulfuric acid magnesium salt (1:1) → HCID 52936282, compound

HRID 2202143Notes

Reaction equation

HRID 2202143 reaction equation
C[O:2][C:3]([C@@:5]12[C:11]([CH3:13])([CH3:12])[C@@H:8]([CH2:9][CH2:10]1)[CH:7]=[C:6]2[C:14]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([C:22]([CH3:30])([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH3:23])=[CH:16][C:15]=1[O:31][CH3:32])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1>[CH3:32][O:31][C:15]1[CH:16]=[C:17]([C:22]([CH3:30])([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH3:23])[CH:18]=[C:19]([O:20][CH3:21])[C:14]=1[C:6]1[C@:5]2([CH2:3][OH:2])[C:11]([CH3:13])([CH3:12])[C@H:8]([CH:7]=1)[CH2:9][CH2:10]2

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 68315188HCID 68315188, compound

Product 1

HCID 52936282HCID 52936282, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Solution of methyl ester 11a 0.790 g (1.79 mmol) in THF 20 ml was cooled to 0° C. After addition of LiAlH4 3.58 ml (3.58 mmol, 1M solution in diethyl ether) the reaction was allowed to warm up to ambient temperature and stirred for 18 hrs. The reaction worked up with a small amount of saturated MgSO4 solution and extracted with ethyl acetate. The organic phase was washed with brine and water, dried over MgSO4 and concentrated in vacuo. The product was purified by silica gel column chromatography (petroleum ether/ether) to give oil 0.460 g (62%), which solidified upon standing at −20° C. to give a yellow solid. mp 49-51° C.; 1H NMR (300 MHz, CDCl3) δ ppm 6.52 (s, 2H), 5.90 (d, J=3.24 Hz, 1H), 3.75 (s, 6H), 3.65 (m, 2H), 2.35 (t, J=3.39, 1H), 2.25 (dd, J=7.29, J=5.01, 1H), 1.93 (m, 1H), 1.53-1.59 (m, 5H), 1.27 (s, 6H), 1.21 (s, 3H), 1.0-1.19 (m, 7H), 0.94 (s, 3H), 0.85 (t, J=6.71 Hz, 3H). Exact mass calculated for C27H42O3 m/e 414.31. found 414.87. Anal. calcd. for C27H42O3: C, 78.21; H, 10.21. Found: C, 78.31; H, 10.31.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with brine and water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by silica gel column chromatography (petroleum ether/ether)

Sources & evidence

ORD record
ord-3b1d1ffeb3584509bcd739b20b539d69
Source dataset
uspto-grants-2016_06
Patent number
US09365534B2

Reaction notes

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