Ethyl acetate hexane → HCID 57904887, compound

HRID 1093100Notes

Reaction equation

HRID 1093100 reaction equation
[CH2:1]([CH:4]1[CH2:8][CH:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][O:5]1)[CH:2]=C.I([O-])(=O)(=O)=[O:18].[Na+].C(OCC)(=O)C.CCCCCC>C1COCC1.O.CCOCC.[Os](=O)(=O)(=O)=O>[CH2:10]([O:9][CH:7]1[CH2:6][O:5][CH:4]([CH2:1][CH:2]=[O:18])[CH2:8]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 23667635Sodium periodateHCID 579051612-Allyl-4-(benzyloxy)tetrahydrofuran

Product 1

HCID 57904887HCID 57904887, compoundYield 79%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-allyl-4-(benzyloxy)tetrahydrofuran (3.1 g, 14.20 mmol) in THF (100 mL) and water (100 mL) was added osmium tetroxide (2 mL, 0.327 mmol) at room temperature. After a few minutes, sodium periodate (7.59 g, 35.5 mmol) was added in small portions over 15 min. After 20 h, the reaction mixture was diluted with ether (200 mL), filtered and the filtrate washed with water (2×50 mL) followed by brine (50 mL), then dried (Na2SO4), filtered and concentrated to give a gray oil. Flash column chromatography on a silica gel column using 15-30% ethyl acetate/hexane (5% increment) gave 2-(4-(benzyloxy)tetrahydrofuran-2-yl)acetaldehyde (2.4624 g, 11.18 mmol, 79% yield) as a colorless liquid consisting of a ˜4:1 mixture of diastereomers. 1H NMR (500 MHz, CDCl3) δ: 9.81 (0.8 H, s), 9.77 (0.2 H, s), 7.23-7.37 (5 H, m), 4.48 (1.6 H, s), 4.41 (0.4 H, s), 4.29-4.31 (1 H, m), 4.23-4.20 (0.8 H, m), 4.12-4.09 (0.2 H, m), 4.04-4.06 (0.8 H, m), 3.90-3.94 (0.2 H, m), 3.73 (0.8 H, dd, J=9.9, 4.7 Hz), 3.64 (0.2 H, dd, J=9.9, 4.7 Hz), 2.82-2.94 (1 H, m), 2.60-2.73 (1 H, m), 2.25-2.39 (1 H, m), 1.77 (0.8 H, m), 1.59-1.69 (0.2 H, m). LCMS (M+H) calcd for C13H17O3: 221.12; found: 221.05.

Workup

  1. waitAfter a few minutes
  2. filtrationfiltered
  3. washthe filtrate washed with water (2×50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a gray oil

Sources & evidence

ORD record
ord-c939dc9a79de43cab2f5cce891826f54
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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