Dichloromethane → 4-((((1,1-Dimethylethyl)(dimethyl)silyl)oxy)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-2-carbaldehyde

HRID 1662531Notes

Reaction equation

HRID 1662531 reaction equation
[CH3:1][C:2]([Si:5]([CH3:26])([CH3:25])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[C:10]([CH2:23][OH:24])[CH:9]=1)([CH3:4])[CH3:3].C(Cl)Cl.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.CC1(C)N([O])C(C)(C)CCC1>CCOC(C)=O>[CH3:4][C:2]([Si:5]([CH3:25])([CH3:26])[O:6][CH2:7][C:8]1[CH:9]=[C:10]([CH:23]=[O:24])[C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[CH:12][CH:13]=1)([CH3:1])[CH3:3]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 2724126TempoHCID 12217721Iodo benzene diacetateHCID 57706179(4-((((1,1-Dimethylethyl)(dimethyl)silyl)oxy)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-2-yl)methanol

Product 1

HCID 577066184-((((1,1-Dimethylethyl)(dimethyl)silyl)oxy)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-2-carbaldehydeYield 87.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 200 mL round bottom flask was charged with 83.18B (1.21 g, 3.21 mmol), DCM (9 mL), iodobenzene diacetate (available from Aldrich) (1.24 g, 3.86 mmol), and TEMPO (available from Aldrich) (0.0502 g, 0.321 mmol). The solution was stirred for 2 hours at room temperature and diluted with EtOAc. The organic phase was washed with saturated aqueous NaHCO3, saturated aqueous Na2S2O3, and brine, dried (MgSO4), and concentrated. The residue was purified by silica gel flash chromatography (0-5% EtOAc/hexane) to afford 83.18C (1.05 g, 87% yield) as a colorless oil.

Workup

  1. washThe organic phase was washed with saturated aqueous NaHCO3, saturated aqueous Na2S2O3, and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel flash chromatography (0-5% EtOAc/hexane)

Sources & evidence

ORD record
ord-86b05b8e30164787a3d4d23d90f58f92
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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