Methylene blue cation → HCID 86591448, compound

HRID 1582692Notes

Reaction equation

HRID 1582692 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](C)=[CH:15][CH2:16][OH:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CN(C1C=CC2N=C3C(=CC(C=C3)=[N+](C)C)SC=2C=1)C.[C:39]1(=[O:45])[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:57]1[CH2:62]CCOO1>CC#N.C(Cl)Cl.C([O-])(O)=O.[Na+]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH:14]=[CH:15][CH:16]3[CH2:62][O:57][C:39]4([CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]4)[O:45][O:17]3)=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 4139Methylene blue cationHCID 6101p-Toluenesulfonic acidHCID 7967CyclohexanoneHCID 19593658CID 19593658HCID 69796258HCID 69796258, compound2×

Product 1

HCID 86591448HCID 86591448, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 3-(4′-bromo-[1,1′-biphenyl]-4-yl)-2-butenol (4f, 500 mg) and methylene blue (5 mg) in CH3CN (35 ml) and CH2Cl2 (35 ml) was photooxygenated at −6° C. for 3.5 h. Cyclohexanone (1 ml) and p-toluenesulfonic acid (60 mg) were added and reaction mixture was left at r.t. for 18 h. The reaction mixture was diluted with saturated NaHCO3 solution (5 ml) and worked up as above and concentrated. Crude product was purified by column chromatography to furnish 320 mg (47% yield, based on allylic alcohol 4f, used) of trioxane 7fc, m.p. 118-120° C.

Workup

  1. customreaction mixture
  2. concentrationconcentrated
  3. customCrude product was purified by column chromatography
  4. customto furnish 320 mg (47% yield

Sources & evidence

ORD record
ord-a40f0c4e35464c97b0882679b1e10841
Source dataset
uspto-grants-2004_05
Patent number
US06737438B2

Reaction notes

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