Cesium carbonate → (S)-3-[4-[4'-(Trifluoromethyl)-3-biphenylylmethoxy]phenyl]-4-hexynoic acid methyl ester

HRID 2375730Notes

Reaction equation

HRID 2375730 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH2:12]Cl)=[CH:5][CH:4]=1.[CH3:19][O:20][C:21](=[O:34])[CH2:22][C@@H:23]([C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1)[C:24]#[C:25][CH3:26].C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[CH3:19][O:20][C:21](=[O:34])[CH2:22][C@@H:23]([C:27]1[CH:28]=[CH:29][C:30]([O:33][CH2:12][C:11]2[CH:10]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:18])([F:17])[F:1])=[CH:4][CH:5]=3)[CH:16]=[CH:15][CH:14]=2)=[CH:31][CH:32]=1)[C:24]#[C:25][CH3:26]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 222801383-(4-Trifluoromethylphenyl)-benzyl chlorideHCID 59855119(3S)-3-(4-Hydroxy-phenyl)-hex-4-ynoic acid methyl ester

Product 1

HCID 59855127(S)-3-[4-[4'-(Trifluoromethyl)-3-biphenylylmethoxy]phenyl]-4-hexynoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

Benzyl chloride 2.3 (28.0 g, 103 mmol) and phenol 1 (21.5 g, 98 mmol) were dissolved in acetone (150 mL) and treated with Cs2CO3 (39.9 g, 122 mmol). The reaction was stirred at 50° C. for 16 hours, filtered, and concentrated to a pale yellow oil which was chromatographed (silica gel, 33% to 66% DCM in hexanes). Eluant containing compound 2.4 was concentrated to a colorless oil (40.0 g).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to a pale yellow oil which
  3. customwas chromatographed (silica gel, 33% to 66% DCM in hexanes)
  4. additionEluant containing compound 2.4
  5. concentrationwas concentrated to a colorless oil (40.0 g)

Sources & evidence

ORD record
ord-7fbd0623a2b940b28836895d82d2cfb5
Source dataset
uspto-grants-2008_12
Patent number
US07465804B2

Reaction notes

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