Hydrochloric Acid → (6-Butylbenzofuran-2-yl)methanol

HRID 629150Notes

Reaction equation

C[O:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[C:12]([CH2:14][CH2:15][CH2:16][CH3:17])[CH:11]=[CH:10][C:8]=2[CH:9]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>CCOCC>[CH2:14]([C:12]1[CH:11]=[CH:10][C:8]2[CH:9]=[C:5]([CH2:3][OH:2])[O:6][C:7]=2[CH:13]=1)[CH2:15][CH2:16][CH3:17]

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl-6-butylbenzofuran-2-carboxylate (118 mg, 0.51 mmol) was dissolved in 2 mL of anhydrous ether, flushed with argon and cooled to 0° C. Powdered lithium aluminum hydride (21 mg, 0.56 mmol) was added and the resulting suspension stirred vigorously for 2 h at 0° C. The mixture was poured into 25 mL of 1 N hydrochloric acid and extracted with ether (3×20 mL). The combined ether extracts were dried over magnesium sulfate, filtered and concentrated. The crude mixture was subjected to chromatography on silica gel with gradient elution (5-20% ethyl acetate in hexanes) to give (6-butylbenzofuran-2-yl)methanol (85 mg, 82%) as an oil. Used without further characterization.

Workup

customflushed with argon
extractionextracted with ether (3×20 mL)
dry with materialThe combined ether extracts were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
washThe crude mixture was subjected to chromatography on silica gel with gradient elution (5-20% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-d5564f04f7894cfb981d899d8ed57b54
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315495B2

Reaction notes

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