Water → HCID 54003692, compound

HRID 654326Notes

Reaction equation

HRID 654326 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([S:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](O)=[O:14])[C:8]#[CH:9].O.[OH-].[Na+]>O1CCCC1>[CH2:7]([S:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[CH2:13][OH:14])[C:8]#[CH:9]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 2054580HCID 2054580, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 54003692HCID 54003692, compoundYield 82,281.102%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of LiAlH4 (6.5 g; 0.17 mmol) in 250 ml of tetrahydrofuran (THF) at 0° C. was added 2-(2-propynylthio)benzoic acid (28.8 g; 0.15 mmol). The reaction mixture was allowed to warm to room temperature. To the reaction mixture was added 6.5 ml of water, then 6.5 ml of 15% NaOH and 13.0 ml of water. The mixture was filtered through diatomaceous earth (Celite,) and concentrated to afford 22 g of the subtitle compound.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth (Celite,)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-2cb72b9f61f4442aa48a0709e6503934
Source dataset
uspto-grants-1992_07
Patent number
US05130485

Reaction notes

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