Tetrahydrofuran → HCID 131723387, compound

HRID 2228395Notes

Reaction equation

HRID 2228395 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][C:5]=1[SiH:11]([CH3:13])[CH3:12])[CH:2]=[CH2:3].[I-].[C:15]([C:20]1C=CC([Zn+])=[CH:22][CH:21]=1)([O:17][CH2:18][CH3:19])=[O:16].[CH2:27]1[CH2:31]OC[CH2:28]1>>[CH2:31]([C:7]1[CH:8]=[CH:9][C:4]([C:1]2[CH:22]=[CH:21][C:20]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:3][CH:2]=2)=[C:5]([SiH:11]([CH3:13])[CH3:12])[CH:6]=1)[CH:27]=[CH2:28]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 131723385HCID 131723385, compoundHCID 178469116HCID 178469116, compound

Product 1

HCID 131723387HCID 131723387, compoundYield 72%

Conditions

Temperature
60 °C

Procedure

To a solution of 5 mol % Pd(Ph3)4 (288 mg, 0.25 mmol) and 1-allyldimethylsilyl-4-iodobenzene (1 Scheme 24, 1.5 g, 5 mmol) in dry THF (10 mL) was added (4-carbethoxyphenyl)zinc iodide (0.5 M solution in THF, 10 mL, 5 mmol). After degassing by bubbling with N2, the reaction mixture was sealed and stirred for 16 h at 60° C. The mixture was treated with saturated NH4Cl (10 mL) and extracted. The organic layer was dried over Na2SO4 and concentrated. The resulting crude product was purified by column chromatography (1:30 ethyl acetate/hexanes) to afford a colorless oil (12 g, 72%); 1H NMR (300 NMz, CDCl3) δ 0.39 (s,6H), 1.46 (t, J=7.5 Hz, 3 H), 1.85 (d, J 8.0 Hz, 2 H), 4.45 (d, J=7.5 Hz, 2 H), 4.94 (s, 1 H), 4.97 (m, 1 H), 5.84 (m, 1 H), 7.65(4 H), 7.70 (d, J=8.0 Hz, 2 H), 8.18 (d, J=8.18 (d, J=8.0 Hz, 2 H); HRMS (EI) calcd for C20H24O2Si 324.1545, found 324.1545.

Workup

  1. customAfter degassing
  2. customby bubbling with N2
  3. customthe reaction mixture was sealed
  4. additionThe mixture was treated with saturated NH4Cl (10 mL)
  5. extractionextracted
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customThe resulting crude product was purified by column chromatography (1:30 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2fff64e97c204b66a4a68ca1bc7bbf53
Source dataset
uspto-grants-2002_07
Patent number
US06416861B1

Reaction notes

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