Sodium Sulfate → HCID 10388777, compound

HRID 363835Notes

Reaction equation

HRID 363835 reaction equation
O1CCCCC1[O:7][C:8](=O)[CH2:9][CH2:10][C@H:11]([C@@H:13]1[C@:30]2([CH3:31])[C@H:16]([C@H:17]3[C@H:27]([CH2:28][CH2:29]2)[C@:25]2([CH3:26])[C:20]([CH2:21][C@@H:22]([O:32][CH:33]4[CH2:38][CH2:37][CH2:36][CH2:35][O:34]4)[CH2:23][CH2:24]2)=[CH:19][CH2:18]3)[CH2:15][CH2:14]1)[CH3:12].[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[O:34]1[CH2:35][CH2:36][CH2:37][CH2:38][CH:33]1[O:32][C@H:22]1[CH2:23][CH2:24][C@@:25]2([CH3:26])[C:20](=[CH:19][CH2:18][C@@H:17]3[C@@H:27]2[CH2:28][CH2:29][C@@:30]2([CH3:31])[C@H:16]3[CH2:15][CH2:14][C@@H:13]2[C@H:11]([CH3:12])[CH2:10][CH2:9][CH2:8][OH:7])[CH2:21]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 10076027HCID 10076027, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10388777HCID 10388777, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Compound 2001 (16.1 g, 30 mmol) in dry tetrahydrofuran (THF, 150 ml) was added to a suspension of LiAlH4 (5.5 g, 145 mmol) in dry THF (200 ml). The suspension was stirred at 0° C. with a mechanical stirrer under argon overnight. The resultant gray slurry was quenched with EtOAc, followed by aqueous saturated Na2SO4 solution. During the addition of the Na2SO4 solution, a white precipitate formed and the solution became clear. Anhydrous Na2SO4 was added, the mixture was stirred for 15 minutes, and then filtered. The filter cake was washed well with ethyl acetate and the filtrate was concentrated in vacuo. The resulting solid was purified by flash chromatography (SiO2, hexanes:EtOAc 5:1) giving compound 2002 as a white solid (12.3 g, 27.7 mmol, 92%). 1H NMR (500 MHz, CDCl3) δ 5.37-5.32 (m, 1H, C-6 H) , 4.72 (brs, 1H, THP methine H), 3.95-3.88 (m, 1H, THP CH2O), 3.62-3.47 (m, 4H, THP CH2O & C-3 H & C-24 H), 1.01 (s, 3H, C-19 H), 0.93 (d, J=6.6 Hz, C-21 H), 0.68 (s, 3H, C-18 H); IR (CHCl3) 3610, 2900 cm-1 ; MS (CI/isobutane) m/z 445 (M+1, 2%), 343 (M+1-THPOH, 100%); m.p. 130°-131° C.

Workup

  1. customThe resultant gray slurry was quenched with EtOAc
  2. additionDuring the addition of the Na2SO4 solution
  3. customa white precipitate formed
  4. stirringthe mixture was stirred for 15 minutes
  5. filtrationfiltered
  6. washThe filter cake was washed well with ethyl acetate
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe resulting solid was purified by flash chromatography (SiO2, hexanes:EtOAc 5:1)

Sources & evidence

ORD record
ord-10925c38637e46879d5a37e36510d1c2
Source dataset
uspto-grants-1999_02
Patent number
US05874597

Reaction notes

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