Water → HCID 20028751, compound

HRID 1722356Notes

Reaction equation

HRID 1722356 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:20][CH:21]([OH:30])[CH2:22][S:23][CH2:24][CH2:25][C:26]([O:28]C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH2:37].[OH-].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]1[C:14]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:20][C:21]([OH:30])([OH:37])[CH2:22][S:23][CH2:24][CH2:25][CH2:26][OH:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 14421499HCID 14421499, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20028751HCID 20028751, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1 g (2.33 mmol) of methyl 7-(2-benzyloxy-3-cyclopentylphenyl)-6-hydroxy-4-thiaheptanoate (Example 1) is dissolved in 3 ml of tetrahydrofuran, and the solution is added dropwise to 250 mg of lithium aluminum hydride in 20 ml of tetrahydrofuran. The mixture is left to stir at room temperature for 30 min and then, with caution, 0.25 ml of water, 0.25 ml of 15% strength sodium hydroxide solution and 0.73 ml of water are successively added. The precipitate is filtered off, the filtrate is washed once with saturated brine and dried over magnesium sulfate, and the solvent is removed by distillation in vacuo. The residue is purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 1:1). 745 mg of 7-(2-benzyloxy-3-cyclopentylphenyl)-6-hydroxy-4-thiaheptane-1,6-diol are obtained.

Workup

  1. waitThe mixture is left
  2. filtrationThe precipitate is filtered off
  3. washthe filtrate is washed once with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent is removed by distillation in vacuo
  6. customThe residue is purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-b170aca1aa6740aaa2c3a9b1d3cb5ecd
Source dataset
uspto-grants-1989_08
Patent number
US04855323

Reaction notes

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