4-Hydroxybiphenyl → HCID 10560973, compound

HRID 1053511Notes

Reaction equation

HRID 1053511 reaction equation
[C:1]([OH:5])(=[O:4])[C:2]#[CH:3].[C:6]1([C:12]2[CH:17]=[CH:16][C:15](O)=[CH:14][CH:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)C.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:15]1[CH:16]=[CH:17][C:12]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[CH:13][CH:14]=1)(=[O:4])[C:2]#[CH:3]

Participants

6

Reactant 3

HCID 71034-HydroxybiphenylHCID 10110Propiolic AcidHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 10560973HCID 10560973, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To an ice cooled and stirred solution of propargylic acid (285 mg, 4.01 mmol) and 4-phenylphenol (693 mg, 4.07 mmol) in dry diethyl ether was added dropwise a solution of N,N′-dicyclohexylcarbodiimide (DCC, 840 mg, 4.07 mmol) and 4-dimethylaminopyridine (DMAP, 3.2 mg, 0.03 mmol) in dry diethyl ether (10 mL) during 2 h under nitrogen atmosphere. Reaction mixture was then stirred at room temperature for 10 h, filtered and the solid was washed with diethyl ether. Then, the combined filtrate was washed with 1 N HCl solution followed by washing with brine and dried with anhydrous Na2SO4. The solvent was removed under reduced pressure to give the crude product that was then purified by column chromatography using ethyl acetate:hexane (1:9) as an eluant to give compound 1 (0.81 mg, 90%). 1H NMR (400 MHz, CDCl3): δ 3.12 (s, 1H), 7.24 (s, 1H), 7.26 (s, 1H), 7.38 (s, 1H), 7.47 (t, J=7.8 Hz, 2H), 7.57 (s, 1H), 7.59 (s, 1H), 7.62 (s, 1H), 7.64 (s, 1H). HRMS ESI (m/z): Calculated for C15H10O2 ([M+H]+): 223.0681. found: 223.0734.

Workup

  1. customReaction mixture
  2. filtrationfiltered
  3. washthe solid was washed with diethyl ether
  4. washThen, the combined filtrate was washed with 1 N HCl solution
  5. washby washing with brine
  6. dry with materialdried with anhydrous Na2SO4
  7. customThe solvent was removed under reduced pressure
  8. customto give the crude product that
  9. customwas then purified by column chromatography

Sources & evidence

ORD record
ord-6a3371ba524b42e789b2ab5ac5a49de0
Source dataset
uspto-grants-2016_07
Patent number
US09393306B2

Reaction notes

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