Toluene → (+/-)-1-(Biphenyl-3-yloxy)-4-(3-pyridyl)-2-butanol

HRID 1600943Notes

Reaction equation

HRID 1600943 reaction equation
[C:1]1(C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:15]1[CH:16]=[C:17]([CH:30]=[CH:31][CH:32]=1)[O:18][CH2:19][CH:20]([OH:29])[CH2:21][CH2:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1.C1(B(O)O)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[C:15]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:32]=[CH:31][CH:30]=[C:17]([O:18][CH2:19][CH:20]([OH:29])[CH2:21][CH2:22][C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[CH:16]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 21830708(+/-)-1-(3-Bromophenoxy)-4-(3-pyridyl)-2-butanol

Product 1

HCID 21830665(+/-)-1-(Biphenyl-3-yloxy)-4-(3-pyridyl)-2-butanol

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

Prepared according to the method described in Example 33a) from toluene (5 ml), aqueous sodium carbonate (2 M, 1 ml), (±)-1-(3-bromophenoxy)-4-(3-pyridyl)-2-butanol (0.25 g), ethanol (1 ml), benzeneboronic acid (0.14 g) and tetrakis(triphenylphosphine)palladium(0) (30 mg) with heating at reflux for 4 hours. The residue obtained after work up was purified by column chromatography over silica eluting with ethyl acetate to give (±)-1-(biphenyl-3-yloxy)-4-(3-pyridyl)-2-butanol as a colourless oil (0.178 g). Conversion to the oxalate salt upon treatment with excess saturated ethereal oxalic gave the title compound as a hygroscopic gum. (0.10 g)

Workup

  1. customPrepared
  2. temperaturewith heating
  3. temperatureat reflux for 4 hours
  4. customThe residue obtained after work
  5. customup was purified by column chromatography over silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-0f1ab88b47734197b88df8544dd7ff3d
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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