Diisobutylaluminum hydride → 3-(Hydroxymethyl)benzofuran-6-ol

HRID 1947497Notes

Reaction equation

HRID 1947497 reaction equation
C([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=2[O:8][CH:7]=1)=O)C.CC(C[AlH]CC(C)C)C>C1COCC1>[OH:3][CH2:4][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=2[O:8][CH:7]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 59152646HCID 59152646, compound

Product 1

HCID 451226643-(Hydroxymethyl)benzofuran-6-olYield 101.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (0° C.) solution of 6-hydroxy-benzofuran-3-carboxylic acid ethyl ester (5.85 g, 28.4 mmol) in THF (250 mL) was added DIBALH as a solution in THF (100 mL, 100 mmol) and the reaction mixture was allowed to warm (rt, 1 h). The reaction was cooled (−78° C.) and treated dropwise with Rochelles salt (120 mL). The resulting mixture was stirred (rt, o/n). The layers were separated and the aqueous layer was extracted with DCM (2×200 mL) and EtOAc (2×200 mL). The organic layers were combined, dried, filtered and concentrated in vacuo to provide the title compound as a white solid (4.72 g, 100%). 1H NMR (500 MHz, CD3OD): 7.53 (s, 1H), 7.45 (d, J=8.4, 1H), 6.85 (d, J=2.1, 1H), 6.76 (dd, J=8.4, 2.1, 1H), 4.70 (s, 2H).

Workup

  1. temperatureThe reaction was cooled (−78° C.)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with DCM (2×200 mL) and EtOAc (2×200 mL)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46171b78973f4caf95c7962c949c6d96
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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