Water → HCID 19366859, compound

HRID 849534Notes

Reaction equation

HRID 849534 reaction equation
C[CH:2]([CH:6]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3](O)=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([S:13]([CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:2][CH2:3][OH:4])(=[O:15])=[O:14])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19366805HCID 19366805, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19366859HCID 19366859, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Part C: To a solution of 5.0 g (15 mmol) of methyl 3-[(4-methoxyphenyl)sulfonyl]-3-phenylpropanoic acid, from Part B in 60 mL of anhydrous THF at zero° C. under nitrogen, was added 16.4 mL (0.6 g, 15 mmol) of a 1.0 M solution of lithium aluminum hydride in THF. After 2 hours, the reaction mixture was cooled to zero° C. and 1.2 mL of water was added, followed by 1.2 mL of 2.5 N sodium hydroxide solution and 3.6 mL of water, the reaction was filtered, the filtrate concentrated in vacuo, ethyl acetate and 5% citric acid solution were added, the organic layer was separated and washed with saturated sodium bicarbonate solution and brine, dried with magnesium sulfate, filtered and concentrated to afford 3.9 grams of pure 3-[(4-methoxyphenyl)sulfonyl]-3-phenylpropan-1-ol, m/z=313 (M+Li).

Workup

  1. temperaturethe reaction mixture was cooled
  2. filtrationthe reaction was filtered
  3. concentrationthe filtrate concentrated in vacuo, ethyl acetate and 5% citric acid solution
  4. additionwere added
  5. customthe organic layer was separated
  6. washwashed with saturated sodium bicarbonate solution and brine
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-05cba0aaec0f405cb7aa1ea1ed46ba6f
Source dataset
uspto-grants-2000_01
Patent number
US06013649

Reaction notes

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