Phosphoric Acid → HCID 10052418, compound

HRID 1269353Notes

Reaction equation

HRID 1269353 reaction equation
[C:1](=[O:35])([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31][N+:32]([O-:34])=[O:33])[O:2][CH2:3]/[C:4](/[C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1)=[C:5](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)\[CH2:6][OH:7].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:38].CC(=CC)C.P(=O)(O)(O)O.[O-]Cl=O.[Na+]>ClCCl.C1COCC1.CC(O)(C)C>[CH3:23][S:20]([C:17]1[CH:18]=[CH:19][C:14](/[C:4](/[CH2:3][O:2][C:1]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31][N+:32]([O-:34])=[O:33])=[O:35])=[C:5](\[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)/[C:6]([OH:38])=[O:7])=[CH:15][CH:16]=1)(=[O:21])=[O:22]

Participants

9

Reactant 5

HCID 1004Phosphoric AcidHCID 105532-Methyl-2-buteneHCID 159087TriacetoxyperiodinaneHCID 23668197Sodium ChloriteHCID 58841165HCID 58841165, compound

Product 1

HCID 10052418HCID 10052418, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.5 g of (2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-en-1-yl 6-(nitrooxy)hexyl carbonate in 100 mL of dichloromethane was treated with 4.5 g of Dess-Martin reagent at 25° C. for 75 min. The reaction was quenched by 1 mL of water, and stirred at RT for 30 min. Then the mixture was filtered through a pad of silica gel and evaporated. The crude thus obtained was dissolved in a solvent mixture of THF and t-BuOH (100 mL/100 mL). To the resulting solution was added 5.3 mL of 2-methyl-2-butene followed by the addition of 13 mL of phosphoric acid (1.2 M soln) and 13 mL of NaClO2 (1M soln). The resulting 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 titled compound as a white solid. 1H NMR (acetone-d6, 500 MHz): δ 11.8 (bs, 1 H), 7.76 (d, 2 H), 7.43 (d, 2 H), 7.17–7.11 (m, 5 H), 5.34 (s, 2 H), 4.52 (t, 2 H), 4.04 (t, 2 H), 3.05 (s, 3 H), 1.71 (m, 2 H), 1.57 (m, 2 H), 1.40 (m, 2 H), 1.34 (m, 2 H).

Workup

  1. customThe reaction was quenched by 1 mL of water
  2. filtrationThen the mixture was filtered through a pad of silica gel
  3. customevaporated
  4. customThe crude thus obtained
  5. stirringThe resulting mixture was stirred at RT for 30 min
  6. customThe organic phase was separated
  7. extractionthe aqueous phase was extracted with EtOAc
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-b0b3aaa7be3747ba8e15cda1fbcfb888
Source dataset
uspto-grants-2007_04
Patent number
US07199154B2

Reaction notes

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