Methylene blue cation → HCID 86759449, compound

HRID 1582691Notes

Reaction equation

HRID 1582691 reaction equation
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([C:7](C)=[CH:8][CH2:9][OH:10])=[CH:3][CH:2]=1.CN(C1C=CC2N=C3C(=CC(C=C3)=[N+](C)C)SC=2C=1)C.[CH3:38][C:39](=[O:50])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49].[O:51]1[CH2:56]CCOO1>C(#N)C.C(Cl)(Cl)Cl.Cl>[CH2:40]([C:39]1([CH3:38])[O:51][CH2:56][CH:9]([CH:8]=[CH:7][C:4]2[CH:3]=[CH:2][C:1]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:6][CH:5]=2)[O:10][O:50]1)[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49]

Participants

8

Reactant 4

HCID 4139Methylene blue cationHCID 225562-DodecanoneHCID 19593658CID 19593658HCID 69475784HCID 69475784, compound2×

Product 1

HCID 86759449HCID 86759449, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 3-([1,1′-biphenyl]-4yl)-2-butenol (4e, 200 mg) and methylene blue (2 mg) in acetonitrile (10 ml) and chloroform (10 ml) was photooxygenated at 0° C. for 3 h. 2-dodecanone (0.5 ml) and hydrochloric acid (2 drops) were added and reaction mixture of left at r.t. for 18 h. The reaction mixture was worked up and concentrated. Crude product was purified by column chromatography on silica gel to furnish 100 mg mg (27% yield, based on allylic alcohol, 4e, used) of trioxane 7ed m.p. 86-90° C.

Workup

  1. customreaction mixture
  2. concentrationconcentrated
  3. customCrude product was purified by column chromatography on silica gel
  4. customto furnish 100 mg mg (27% yield

Sources & evidence

ORD record
ord-4920626c5af44dcfb3f64be231574466
Source dataset
uspto-grants-2004_05
Patent number
US06737438B2

Reaction notes

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