Water → HCID 23130526, compound

HRID 2080091Notes

Reaction equation

HRID 2080091 reaction equation
[CH3:1][C:2]1[S:6][C:5]([CH2:7][C:8]2[S:12][C:11]([CH:13]=[O:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(OCC)(=O)C>O1CCCC1>[CH3:1][C:2]1[S:6][C:5]([CH2:7][C:8]2[S:12][C:11]([CH2:13][OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 23130569HCID 23130569, compound

Product 1

HCID 23130526HCID 23130526, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(5-methyl-thiophen-2-ylmethyl)-thiophene-2-carbaldehyde described in Preparation Example 66 (790 mg, 3.56 mmol) in tetrahydrofuran (5 mL) was added lithium aluminum hydride (41 mg, 1.06 mmol), and the mixture was stirred at room temperature for 10 minutes. Water and ethyl acetate were added to the reaction mixture, which was then partitioned, the organic layer was filtered with a glass filter lined with silica gel, the filtrate was evaporated in vacuo, and the title compound (640 mg, 2.86 mmol, 80.3%) was obtained as a light brown oil.

Workup

  1. customwas then partitioned
  2. filtrationthe organic layer was filtered with a glass
  3. filtrationfilter
  4. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-27febe8c21cf44808c4d8473a49d358e
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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