tert-Butyl 3-iodobenzoate → HCID 18386974, compound

HRID 2298507Notes

Reaction equation

HRID 2298507 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[I-].[CH3:16][O:17][C:18]([CH2:20][CH2:21][CH2:22][Zn+])=[O:19]>C1COCC1.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:8]([O:7][C:5]([C:4]1[CH:3]=[C:2]([CH2:22][CH2:21][CH2:20][C:18]([O:17][CH3:16])=[O:19])[CH:14]=[CH:13][CH:12]=1)=[O:6])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 18386959tert-Butyl 3-iodobenzoateHCID 178500475HCID 178500475, compound

Product 1

HCID 18386974HCID 18386974, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl 3-iodobenzoate (2 g, 6.58 mmol) and tetrakis(triphenylphosphine)palladium(0) (250 mg, 0.329 mmol) in THF (10 ml) was treated with a freshly prepared 3-methoxycarbonylpropylzinc iodide (0.25 M in THF, 27 ml, 6.58 mmol). The mixture was stirred at room temperature for 3 hours, quenched with saturated aqueous ammonium chloride (5 ml) and extracted with diethyl ether. The organic phase was washed with saturated aqueous ammonium chloride, brine, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel (hexane:ethyl acetate=9:1) to give the title material (0.73 g, 40%) as a colorless oil.

Workup

  1. customquenched with saturated aqueous ammonium chloride (5 ml)
  2. extractionextracted with diethyl ether
  3. washThe organic phase was washed with saturated aqueous ammonium chloride, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-510db93df2df442081aeee32e9592326
Source dataset
uspto-grants-2002_12
Patent number
US06492550B2

Reaction notes

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