Water → HCID 59300582, compound

HRID 2235588Notes

Reaction equation

HRID 2235588 reaction equation
[C:1]1([CH3:22])[CH:6]=[CH:5][C:4]([C:7]2[S:11][C:10]([C:12]3C=CC=CC=3C(OC)=O)=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH2:29].[OH-].[Na+]>C1COCC1>[C:1]1([CH3:22])[CH:6]=[CH:5][C:4]([C:7]2[S:11][C:10]([CH2:12][OH:29])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86619682HCID 86619682, compound

Product 1

HCID 59300582HCID 59300582, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (5-p-tolylthiophen-2-yl)benzoate (5.0 mmol) in THF (20 mL) at 0° C. was slowly added LAH (1.0 M in THF, 6.0 mL). The reaction was then stirred at room temperature for 3 hours, and water (0.24 mL), 15% aqueous NaOH (0.24 mL), and water (0.72 mL) were added to the reaction mixture. After 30 minutes, the reaction mixture was filtered through celite and concentrated to give the pure product 13.1 (0.95 g). MS ESI (pos.) m/e 205.0 (M+H).

Workup

  1. customat 0° C.
  2. waitAfter 30 minutes
  3. filtrationthe reaction mixture was filtered through celite and
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d91b9415b53148fb8e0449b75e78f639
Source dataset
uspto-grants-2010_05
Patent number
US07714008B2

Reaction notes

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