Benzene, 1,3-diiodo- → HCID 68108894, compound

HRID 2179369Notes

Reaction equation

HRID 2179369 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([I:8])[CH:3]=1.C([Li])CCC.[O:14]1[CH2:18][CH2:17][C:16](=[O:19])[CH2:15]1.[NH4+].[Cl-]>C1COCC1>[I:8][C:4]1[CH:3]=[C:2]([C:16]2([OH:19])[CH2:17][CH2:18][O:14][CH2:15]2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 12270Benzene, 1,3-diiodo-HCID 25517Ammonium ChlorideHCID 5293923-OxotetrahydrofuranHCID 178418339Butyllithium

Product 1

HCID 68108894HCID 68108894, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1,3-diiodobenzene (3.0 g, 9.09 mmol) in dry THF (40 mL) was cooled to −78° C. under a nitrogen before addition of n-butyl lithium (1.6 M in hexane, 5.6 mL, 9.09 mmol) dropwise over 10 min. The reaction mixture was stirred for 30 min and then a solution of dihydrofuran-3(2H)-one (782 mg, 9.09 mmol) in THF (3 mL) added over 5 min. The reaction mixture was stirred for 1 h at −78° C. then poured into saturated NH4Cl solution. The mixture was extracted with ethyl acetate and the organic layer dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 9:1 hexanes/ethyl acetate) to give 3-(3-iodophenyl)tetrahydrofuran-3-ol (2.0 g, 76%) as a colorless liquid: 1H NMR (CDCl3, 300 MHz) δ 7.87 (t, J=1.8 Hz, 1H), 7.64 (td, J=7.8 Hz, 1H), 7.45 (td, J=7.8 Hz, 1H), 7.10 (t, J=8.1 Hz, 1H), 4.26-4.06 (m, 2H), 3.98-3.82 (m, 2H), 2.46-2.32 (m, 1H), 2.30-2.21 (m, 1H).

Workup

  1. stirringThe reaction mixture was stirred for 1 h at −78° C.
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe organic layer dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography (SiO2, 9:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-d26d48c996d145739255ee89c703729a
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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