5-Formyl-2-thiopheneboronic acid → 5-Hydroxymethylthiophene-2-boronic acid

HRID 1023316Notes

Reaction equation

HRID 1023316 reaction equation
[CH:1]([C:3]1[S:7][C:6]([B:8]([OH:10])[OH:9])=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[S:7][C:6]([B:8]([OH:10])[OH:9])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 27734305-Formyl-2-thiopheneboronic acidHCID 4311764Sodium borohydride

Product 1

HCID 43742655-Hydroxymethylthiophene-2-boronic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-formylthiophen-2-ylboronic acid (15.6 mg, 0.1 mmol) in MeOH (0.5 mL) was added excess amount of NaBH4. The mixture was stirred at room temperature for 2 hours and evaporated under reduced pressure to afford crude 5-(hydroxymethyl)thiophen-2-ylboronic acid, which was used in step E without further purification.

Workup

  1. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e9c82b02981d4490b8f02ad00d96b47f
Source dataset
uspto-grants-2014_05
Patent number
US08722692B2

Reaction notes

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