Water → HCID 59300582, compound

HRID 1675248Notes

Reaction equation

HRID 1675248 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-18a4bef5fe704f4fa0179d29dac9db98
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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