Tetrahydrofuran → HCID 131723386, compound

HRID 2228394Notes

Reaction equation

HRID 2228394 reaction equation
C([C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][C:5]=1[SiH:11]([CH3:13])[CH3:12])C=C.[Br-].[CH2:15]([O:17][C:18](=[O:22])[CH2:19][CH2:20][Zn+])[CH3:16].[CH2:23]1[CH2:27]OC[CH2:24]1>>[CH2:27]([C:7]1[CH:8]=[CH:9][C:4]([CH2:20][CH2:19][C:18]([O:17][CH2:15][CH3:16])=[O:22])=[C:5]([SiH:11]([CH3:12])[CH3:13])[CH:6]=1)[CH:23]=[CH2:24]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 131723385HCID 131723385, compoundHCID 178471816HCID 178471816, compound

Product 1

HCID 131723386HCID 131723386, compoundYield 80%

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 3-ethoxy-3-oxopropylzinc bromide (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 (1.1 g, 80%); 1H NMR (300 MHz, CDCl3) δ 0.34 (s, 6 H), 1.29 (d, J=7.2 Hz, 3 H), 1.81 (d, J=7.8 Hz, 2 H), 2.68 (t, J=7.7 Hz, 2 H), 3.02 (t, J=7.7 Hz, 2 H), 4.18 (q, J=7.2 Hz, 2 H), 4.90 (s, 1 H), 4.94 (d, J=7.8 Hz, 1 H), 5.82 (m, 1 H), 7.27 (d, J=7.8 Hz, 2 H), 7.51 (d, J=7.8 Hz, 2 H); 13C NMR (75 MHz, CDCl3) −3.1. 14.5 24.0, 31.2, 36.0, 60.6, 113.7, 128.1, 134.1, 134.9, 136.4, 141.7, 173.0; HRMS (EI) calcd for C16H24O2Si 276.1545, found 276.1548.

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-ce904b17fe1a493ca9b9fbb7f375caa7
Source dataset
uspto-grants-2002_07
Patent number
US06416861B1

Reaction notes

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