Citric Acid → 5-(Hydroxymethyl)furan-2-carbonitrile

HRID 1952850

Reaction equation

[BH4-].[Na+].[C:3]([C:5]1[O:9][C:8]([CH:10]=[O:11])=[CH:7][CH:6]=1)#[N:4].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C.O>[OH:11][CH2:10][C:8]1[O:9][C:5]([C:3]#[N:4])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -30 °C

Procedure

2.34 g (62 mmol) of sodium borohydride were added in portions to a solution of 30 g (0.25 mol) of 5-cyanofuran-2-carbaldehyde in 500 ml of absolute ethanol at -30° C. The solution was stirred at -30° C. for 2 hours and, while cooling, was adjusted to pH 7 with a 5% strength citric acid solution in water. The reaction mixture was concentrated under water pump vacuum, saturated sodium chloride solution was added to the residue, the mixture was extracted several times with 150 ml of diethyl ether each time, the combined organic phases were dried over magnesium sulfate, the desiccant was filtered off, and the solvent was distilled off under water pump vacuum at room temperature. This resulted in 27 g (22 mol, 88%) of the title compound as a dark red oil, which was employed without further purification in the following reactions. 1H-NMR (250 MHz, d6 -DMSO): δ=4.4 (m, 2H), 5.6 (bs, 1H), 6.6 (d, 1H), 7.5 (d, 1H).

Workup

temperaturewhile cooling
concentrationThe reaction mixture was concentrated under water pump vacuum, saturated sodium chloride solution
additionwas added to the residue
extractionthe mixture was extracted several times with 150 ml of diethyl ether each time
dry with materialthe combined organic phases were dried over magnesium sulfate
filtrationthe desiccant was filtered off
distillationthe solvent was distilled off under water
customat room temperature

Sources & evidence

ORD record: ord-595a70d2fddd4cb0852a24aab3c4685d
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06114358

Linked notes

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