Diethyl 6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxylate → (5-Methyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridin-2-yl)-methanol

HRID 1158881Notes

Reaction equation

HRID 1158881 reaction equation
C([O:3][C:4]([C:6]1[S:14][C:13]2[CH2:12][CH2:11][N:10]([C:15](OCC)=O)[CH2:9][C:8]=2[CH:7]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:15][N:10]1[CH2:11][CH2:12][C:13]2[S:14][C:6]([CH2:4][OH:3])=[CH:7][C:8]=2[CH2:9]1

Participants

4

Reactant 2

HCID 14254905Diethyl 6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 21941480(5-Methyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridin-2-yl)-methanolYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

6,7-Dihydro-4H-thieno[3,2-c]pyridine-2,5-dicarboxylic acid diethyl ester (46 gram, 163 mmol) was dissolved in 200 ml THF. The solution was injected LAH (1M, THF) 300 ml at 23° C. Then it was stirred at 23° C. for 18 hrs. The reaction was quenched with 10 ml water and dried directly over sodium sulfate. Filter and concentrate yielded 29.3 gram (160 mmol, 98%) crude product.

Workup

  1. customat 23° C
  2. customThe reaction was quenched with 10 ml water
  3. dry with materialdried directly over sodium sulfate
  4. filtrationFilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-9c1fa148fc714904aa753095ca215dee
Source dataset
uspto-grants-2010_10
Patent number
US07812014B2

Reaction notes

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