4-Hydroxybiphenyl → HCID 18444646, compound

HRID 1786579Notes

Reaction equation

HRID 1786579 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[CH2:7][OH:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:28]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:33]=[CH:32][C:31](O)=[CH:30][CH:29]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(OCC)C>[C:28]1([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:33]=[CH:32][C:31]([O:8][CH2:7][C:6]2[CH:5]=[CH:4][O:3][C:2]=2[CH3:1])=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 71034-HydroxybiphenylHCID 11776TriphenylphosphineHCID 2777165(2-methylfuran-3-yl)methanolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 18444646HCID 18444646, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of (2-methyl-furan-3-yl)-methanol (1) (5.0 g) in diethyl ether (75 mL) was cooled to 0° C. with stirring and treated with triphenylphosphine (12.85 g) and biphenyl-4-ol (7.59 g). The resulting solution was then treated drop-wise with diisopropylazodicarboxylate (9.75 mL). After stirring for 10 minutes at 0° C. the reaction mixture was allowed to warm to room temperature and then stirred for a further 3 hours. The reaction mixture was then filtered and concentrated in vacuo. The residue was purified by flash chromatography, eluting with diethyl ether/petroleum ether (1:19 by volume), to give compound 44 as a white solid (7.0 g). LC/MS System A: Rt=4.38 mins.

Workup

  1. stirringAfter stirring for 10 minutes at 0° C. the reaction mixture
  2. stirringstirred for a further 3 hours
  3. filtrationThe reaction mixture was then filtered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography
  6. washeluting with diethyl ether/petroleum ether (1:19 by volume)

Sources & evidence

ORD record
ord-6c2940245aaf4bbfa62e61b4eb37787a
Source dataset
uspto-grants-2009_03
Patent number
US07507754B2

Reaction notes

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