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

HRID 2266845
Notes
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Reaction equation

HRID 2266845 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 71034-HydroxybiphenylHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 184446624-Hydroxymethyl-5-methyl-furan-2-carbonitrile

Product 1

HCID 184446574-(Biphenyl-4-yloxymethyl)-5-methyl-furan-2-carbonitrileYield 79.2%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

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

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

Sources & evidence

ORD record
ord-1bd586cb84c9403a9ef265b3640e8252
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07858644B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes