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

HRID 1907718Notes

Reaction equation

HRID 1907718 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+]>C(O)(C)C>[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 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 5-formylthiophen-2-ylboronic acid 185 (1.096 g, 7.03 mmol) in isopropanol (10 mL), stirred at 0° C., was treated with solid sodium borohydride (0.336 g, 8.88 mmol) added portion-wise at 0° C. then stirred for 75 min. The reaction was quenched with acetone and concentrated to give compound 186 (used directly in Step 2).

Workup

  1. additionadded portion-wise at 0° C.
  2. stirringthen stirred for 75 min
  3. customThe reaction was quenched with acetone
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-da55a17eb1c64fc9b09125e1ca4e53ac
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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