4-Hydroxybiphenyl → 4-(Biphenyl-4-yloxymethyl)-5-methyl-furan-2-carbonitrile

HRID 1786620Notes

Reaction equation

CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:15][CH2:16][C:17]1[CH:18]=[C:19]([C:23]#[N:24])[O:20][C:21]=1[CH3:22].[C:25]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:25]1([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:30]=[CH:29][C:28]([O:15][CH2:16][C:17]2[CH:18]=[C:19]([C:23]#[N:24])[O:20][C:21]=2[CH3:22])=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Diisopropylazodicarboxylate (1.84 g, 10.6 mmoles) was added to a solution of 4-hydroxymethyl-5-methyl-furan-2-carbonitrile (147) (1.32 g, 9.6 mmoles), biphenyl-4-ol (1.63 g, 9.6 mmoles) and triphenylphosphine (4.3 g, 16.35 mmoles) in tetrahydrofuran (50 mL) with stirring and cooling to 0° C. under an argon atmosphere. After 5 minutes, the cooling was removed and the mixture stirred at room temperature for 16 h. The solvent was evaporated and the residue partitioned between ethyl acetate and water. The ethyl acetate phase was washed with brine and dried. After the solvent was evaporated, the residue was purified by flash chromatography (silica, gradient elution with 5% to 10% ethyl acetate in cyclohexane) to afford compound 148 as a white solid (2.2 g). IR (powder) CN st. 2225 cm−1.

Workup

customthe cooling was removed
stirringthe mixture stirred at room temperature for 16 h
customThe solvent was evaporated
customthe residue partitioned between ethyl acetate and water
washThe ethyl acetate phase was washed with brine
customdried
customAfter the solvent was evaporated
customthe residue was purified by flash chromatography (silica, gradient elution with 5% to 10% ethyl acetate in cyclohexane)

Sources & evidence

ORD record: ord-27f5cc3427694e1da2beab85727cff68
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507754B2

Reaction notes

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