Boron trifluoride → HCID 66699590, compound

HRID 1161068Notes

Reaction equation

HRID 1161068 reaction equation
[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16](O)[C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])=[CH:12][CH:11]=2)=[C:6]([C:28]([F:31])([F:30])[F:29])[C:5]=1[OH:32])(=[O:3])[CH3:2].[SiH](CC)(CC)CC.B(F)(F)F>C(Cl)Cl>[C:1]([C:4]1[CH:27]=[CH:26][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])=[CH:12][CH:11]=2)=[C:6]([C:28]([F:30])([F:31])[F:29])[C:5]=1[OH:32])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 12052TriethylsilaneHCID 57884464HCID 57884464, compound

Product 1

HCID 66699590HCID 66699590, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-{[4-(4-acetyl-3-hydroxy-2-trifluoromethyl-phenoxymethyl)-phenyl]-hydroxy-methyl}-benzonitrile (211 mg, 0.48 mmol) in anhydrous CH2Cl2 (5 mL) at room temperature under Ar is added Et3SiH (0.61 mL, 3.8 mmol) and BF3.ether complex (0.12 mL, 0.96 mmol). The reaction mixture is stirred at room temperature for 2 h and quenched into saturated aqueous NH4Cl (20 mL). The aqueous mixture is extracted with CH2Cl2 (3×25 mL). The organic layers are combined, washed with brine, dried over sodium sulfatesodium sulfate, and concentrated. The residue is purified by flash column chromatography using 50% ethyl acetate/hexane as eluent to give the title compound (108 mg, 53%). LC-MS (m/e): 424 (M−1)

Workup

  1. customquenched into saturated aqueous NH4Cl (20 mL)
  2. extractionThe aqueous mixture is extracted with CH2Cl2 (3×25 mL)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfatesodium sulfate
  5. concentrationconcentrated
  6. customThe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-b630e77d08fb498d99837bcdf9fe6246
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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