Water → HCID 18674435, compound

HRID 1636001Notes

Reaction equation

HRID 1636001 reaction equation
[CH2:1]([Si:3]([CH2:21][CH3:22])([CH2:19][CH3:20])[O:4][CH:5]([CH2:9][CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:6][CH:7]=C)[CH3:2].C[N+]1([O-])CC[O:27]CC1.O.I([O-])(=O)(=O)=O.[Na+]>O1CCCC1.[Os](=O)(=O)(=O)=O>[CH2:1]([Si:3]([CH2:21][CH3:22])([CH2:19][CH3:20])[O:4][CH:5]([CH2:9][CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:6][CH:7]=[O:27])[CH3:2]

Participants

7

Reactant 4

HCID 962Water2×HCID 82029Methyl morpholine oxideHCID 18674439HCID 18674439, compoundHCID 23667635Sodium periodate

Product 1

HCID 18674435HCID 18674435, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10.0 g (31.2 mmol) of 4-Triethylsilyloxy-6-benzyloxy-1-hexene in 310 mL of tetrahydrofuran at 0°C. were added 4.38 g (37.4 mmol) of 4-methylmorpholine N-oxide, 6.24 mL (1.248 mmol) of osmium tetroxide (0.2M in benzene) and 45 mL of water and stirred overnight at room temperature. To the mixture at 0° C. were added 185 mL of water and 20.02 g (93.6 mmol) of sodium periodate and stirred at room temperature for 1 hour, followed by partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated for the next reaction. 1H NMR (CDCl3): δ 9.79 (t, J=2.4 Hz, 1H, CH═O), 7.35-7.31 (m, 5H, ArH), 4.51 (d, J=12.0 Hz, 1H, ArCH2O), 4.46 (d, J=12.0 Hz, 1H, ArCH2O), 4.40 (p, J=6.0 Hz, 1H, CH—O), 3.55 (m, 2H, CH2—O), 2.56 (m, 2H, CH2C═O), 1.85 (m, 2H, CH2), 0.94 (t, J=8.1 Hz, 9H, TES CH3), 0.59 (q, J=8.1 Hz, 6H, TES CH2). 13C NMR (CDCl3): δ 201.94, 138.14, 128.31, 127.60, 127.55, 72.99, 66.31, 65.49, 51.14, 37.71, 6.84, 4.88.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. customby partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated for the next reaction

Sources & evidence

ORD record
ord-d60ff494bc1e4e5e947defee71631b01
Source dataset
uspto-grants-2003_01
Patent number
US06512003B2

Reaction notes

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