Water → HCID 11753385, compound

HRID 1437586Notes

Reaction equation

HRID 1437586 reaction equation
[C:1](=[O:38])([O:16][CH2:17]/[C:18](/[C:28]1[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:30][CH:29]=1)=[C:19](/[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)\[CH2:20][OH:21])[O:2][CH2:3][CH2:4][CH2:5][CH:6]([O:12][N+:13]([O-:15])=[O:14])[CH2:7][O:8][N+:9]([O-:11])=[O:10].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:41].O>ClCCl>[N+:13]([O:12][CH:6]([CH2:7][O:8][N+:9]([O-:11])=[O:10])[CH2:5][CH2:4][CH2:3][O:2][C:1]([O:16][CH2:17]/[C:18](/[C:28]1[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:35])=[O:36])=[CH:30][CH:29]=1)=[C:19](/[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)\[C:20]([OH:41])=[O:21])=[O:38])([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 57941619HCID 57941619, compound

Product 1

HCID 11753385HCID 11753385, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4.5 g of 4,5-bis(nitrooxy)pentyl (2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-en-1-yl carbonate in 50 mL of dichloromethane, 4.13 g of Dess-Martin reagent was added and the resulted mixture was stirred at 25° C. for 45 min. Then 250 uL of water was added and the mixture was stirred at RT for 15 min. Then the mixture was filtered through a pad of silica gel and evaporated. The crude was dissolved in a mixture of THF and t-BuOH (25 mL/25 mL). To this solution was added 6.8 mL of 2-methyl-2-butene followed by the addition of 20 mL of phosphoric acid (1.2M soln) and 20 mL of NaClO2 (1M soln). The resulted mixture was stirred at RT for 30 min. The organic phase was separated and the aqueous phase was extracted with EtOAc. The organic phases were combined, dried over Na2SO4, filtered, and then evaporated. The crude was purified by flash chromatography to afford 2.6 g of the titled compound as white solid. 1H NMR (acetone-d6, 500 MHz): δ 7.77 (d, 2H), 7.44 (d, 2H), 7.17 (s, 3H), 7.12 (t, 2H), 5.51 (s, 1H), 5.35 (s, 2H), 5.00 (dd, 1H), 4.72 (dd, 1H), 4.13-4.10 (m, 2H), 3.06 (s, 3H), 1.87-1.80 (m, 4H).

Workup

  1. stirringthe mixture was stirred at RT for 15 min
  2. filtrationThen the mixture was filtered through a pad of silica gel
  3. customevaporated
  4. dissolutionThe crude was dissolved in a mixture of THF and t-BuOH (25 mL/25 mL)
  5. additionTo this solution was added 6.8 mL of 2-methyl-2-butene
  6. additionfollowed by the addition of 20 mL of phosphoric acid (1.2M soln) and 20 mL of NaClO2 (1M soln)
  7. stirringThe resulted mixture was stirred at RT for 30 min
  8. customThe organic phase was separated
  9. extractionthe aqueous phase was extracted with EtOAc
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. customevaporated
  13. customThe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-7ff7848fafa44a1396178466f106ec7d
Source dataset
uspto-grants-2009_11
Patent number
US07622501B2

Reaction notes

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