Phosphoric Acid → HCID 10255058, compound

HRID 1269348Notes

Reaction equation

HRID 1269348 reaction equation
[N+:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13]/[C:14](/[C:24]1[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1)=[C:15](/[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)\[CH:16]=[O:17])=[O:11])([O-:3])=[O:2].CC(=CC)C.P(=O)(O)(O)[OH:40].[O-]Cl=O.[Na+]>CC(O)(C)C.C1COCC1>[CH3:33][S:30]([C:27]1[CH:28]=[CH:29][C:24](/[C:14](/[CH2:13][O:12][C:10](=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][O:4][N+:1]([O-:3])=[O:2])=[C:15](\[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)/[C:16]([OH:40])=[O:17])=[CH:25][CH:26]=1)(=[O:32])=[O:31]

Participants

7

Reactant 4

HCID 1004Phosphoric AcidHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 58841161HCID 58841161, compound

Product 1

HCID 10255058HCID 10255058, compound

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4.3 g of (2Z)-2-[4-(methylsulfonyl)phenyl]-4-oxo-3-phenylbut-2-enyl 6-(nitrooxy)hexanoate in a solvent mixture of 50 mL of THF with 50 mL of t-BuOH, 5 mL of 2-methyl-2-butene was added followed by the addition of 20 mL of 2 M phosphoric acid and 20 mL of 1 M of NaClO2. The resulting mixture was stirred at rt for 15 min. The organic phases were 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 over silica gel (5–100% EtOAc/hexane) to afford 3.8 g of the titled compound as white solid. 1H NMR (acetone-d6, 500 M Hz): δ 7.79 (d, 2H), 7.45 (d, 2 H), 7.22–7.15 (m, 3 H), 7.15–7.10 (m, 2 H), 5.31 (s, 2 H), 4.51 (t, 2 H), 3.07 (s, 3 H), 2.23 (t, 2 H), 1.72–1.65 (m, 2 H), 1.52–1.45 (m, 2 H), 1.37–1.29 (m, 2 H).

Workup

  1. additionwas added
  2. customThe organic phases were separated
  3. extractionthe aqueous phase was extracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude was purified by flash chromatography over silica gel (5–100% EtOAc/hexane)

Sources & evidence

ORD record
ord-27331bdc53f344ecb790de92b1668292
Source dataset
uspto-grants-2007_04
Patent number
US07199154B2

Reaction notes

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