Ethyl Acetate → HCID 86653781, compound

HRID 1021208Notes

Reaction equation

HRID 1021208 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:11]([CH3:25])[C:10]=1[CH2:26][CH2:27][CH2:28][CH2:29][OH:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].CCOC(C)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:11]([CH3:25])[C:10]=1[CH2:26][CH2:27][CH2:28][CH:29]=[O:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 86653780HCID 86653780, compound

Product 1

HCID 86653781HCID 86653781, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 4-(2,5-bis(benzyloxy)-3,4,6-trimethylphenyl)butan-1-ol (640 mg, 1.58 mmol) in 10 mL CH2Cl2 at 0° C. was treated with a suspension of Dess-martin periodonate (860 mg, 2.03 mmol) in CH2Cl2 (4 mL) and the pale yellow cloudy solution stirred at room temperature for 1.25 h. The cloudy white solution was poured over a solution of 10 mL 1.0 M NaHCO3 containing ˜0.5 g Na2S2O3 and 20 mL EtOAc added, the layers separated and the aqueous phase extracted 3×20 mL EtOAc. The combined organics were washed with 20 mL saturated aqueous NaCl, dried over Na2SO4 and concentrated to a yellow-white solid. The solid was dissolved into 5 mL EtOAc, filtered and the residual solids rinsed with EtOAc. The combined washings were stored overnight at 2° C., concentrated and purified by flash chromatography (gradient elution, 0-20% EtOAc/heptanes) collecting 530 mg of 4-(2,5-bis(benzyloxy)-3,4,6-trimethylphenyl)butanal. MS M++H at 403 m/z; 1H NMR (400 MHz, CDCl3) δ=9.67 (t, 1 H), 7.52-7.48 (m, 2 H), 7.45-7.36 (m, 6 H), 4.75 (s, 2 H), 4.74 (s, 2 H), 2.69 (t, 2 H), 2.44 (td, 2 H), 2.27 (s, 3 H), 2.24 (s, 6 H), 1.84 (pent, 2 H) ppm.

Workup

  1. additionadded
  2. customthe layers separated
  3. extractionthe aqueous phase extracted 3×20 mL EtOAc
  4. washThe combined organics were washed with 20 mL saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to a yellow-white solid
  7. dissolutionThe solid was dissolved into 5 mL EtOAc
  8. filtrationfiltered
  9. washthe residual solids rinsed with EtOAc
  10. waitThe combined washings were stored overnight at 2° C.
  11. concentrationconcentrated
  12. custompurified by flash chromatography (gradient elution, 0-20% EtOAc/heptanes)
  13. customcollecting 530 mg of 4-(2,5-bis(benzyloxy)-3,4,6-trimethylphenyl)butanal

Sources & evidence

ORD record
ord-e6f0f0d7d42e46b8a36d66228d4a4fd4
Source dataset
uspto-grants-2014_05
Patent number
US08716527B2

Reaction notes

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