Phosphoric Acid → HCID 18448169, compound

HRID 1269354Notes

Reaction equation

HRID 1269354 reaction equation
[C:1](=[O:32])([O:10][CH2:11]/[C:12](/[C:22]1[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=1)=[C:13](/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)\[CH2:14][OH:15])[O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][Br:9].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:35].CC(=CC)C.P(=O)(O)(O)O.[O-]Cl=O.[Na+]>ClCCl.C1COCC1.CC(O)(C)C.O>[Br:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][O:2][C:1]([O:10][CH2:11]/[C:12](/[C:22]1[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:29])=[O:30])=[CH:24][CH:23]=1)=[C:13](/[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)\[C:14]([OH:35])=[O:15])=[O:32]

Participants

10

Reactant 5

HCID 1004Phosphoric AcidHCID 105532-Methyl-2-buteneHCID 159087TriacetoxyperiodinaneHCID 23668197Sodium ChloriteHCID 58841178HCID 58841178, compound

Product 1

HCID 18448169HCID 18448169, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 12 g of 6-bromohexyl (2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-en-1-yl carbonate in 125 mL of dichloromethane was added 12.1 g of Dess-Martin reagent; the resulting mixture was stirred at 25° C. for 2 h. Then 1 mL of water was added and the mixture was stirred at RT for 30 min. 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 this solution was added 16 mL of 2-methyl-2-butene followed by the addition of 40 mL of phosphoric acid (1.2M soln) and 40 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 white solid.

Workup

  1. stirringthe mixture was stirred at RT for 30 min
  2. filtrationThe 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-0d0f1f6c4483408486815f1885d7aacd
Source dataset
uspto-grants-2007_04
Patent number
US07199154B2

Reaction notes

Loading…