Water → (6-Methoxy-benzo[b]thiophen-2-yl)-methanol

HRID 1171228Notes

Reaction equation

HRID 1171228 reaction equation
O1CCCC1.C([O:8][C:9]([C:11]1[S:15][C:14]2[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:13]=2[CH:12]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)(=O)C>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:13]2[CH:12]=[C:11]([CH2:9][OH:8])[S:15][C:14]=2[CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 11831419Ethyl 6-methoxybenzo[b]thiophene-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 57608293(6-Methoxy-benzo[b]thiophen-2-yl)-methanolYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a tetrahydrofuran (100 mL) solution of (6-methoxy-benzo[b]-thiophene-2-carboxylic acid ethyl ester (5.0 g, 21.1 mmol) described in Production Example 77-1-1 was added lithium aluminum hydride (2.0 g, 52.8 mmol). The suspension was stirred at room temperature for 30 minutes. The reaction mixture was distributed between water and ethyl acetate. The organic layer was separated followed by drying over anhydrous magnesium sulfate and filtering. The residue was concentrated under a reduced pressure to obtain the title compound (4.1 g, quantitative).

Workup

  1. customThe organic layer was separated
  2. dry with materialby drying over anhydrous magnesium sulfate
  3. filtrationfiltering
  4. concentrationThe residue was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-6644c6f6b7314d86b60111c5209d7b17
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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