Water → Cladrin

HRID 644151Notes

Reaction equation

HRID 644151 reaction equation
B(F)(F)F.[CH3:5]COCC.CS(Cl)(=O)=O.O.[OH:16][C:17]1[CH:22]=[C:21]([OH:23])[CH:20]=[CH:19][C:18]=1[C:24](=[O:36])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=1>CN(C=O)C>[CH3:35][O:34][C:28]1[CH:27]=[C:26]([C:25]2[C:24](=[O:36])[C:18]3[C:17](=[CH:22][C:21]([OH:23])=[CH:20][CH:19]=3)[O:16][CH:5]=2)[CH:31]=[CH:30][C:29]=1[O:32][CH3:33]

Participants

6

Reactant 4

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 31297Methanesulfonyl chlorideHCID 6890381-(2,4-Dihydroxyphenyl)-2-(3,4-dimethoxyphenyl)ethanone

Product 1

HCID 5748605Cladrin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In a similar manner to Example 2.1 above, 1-(2,4-dihydroxyphenyl)-2-(3,4-dimethoxy-phenyl)-ethanone dissolved in DMF had added boron trifluoride diethyl etherate followed by methanesulfonyl chloride in DMF. Addition of water to the reaction mixture afforded 3-(3,4-dimethoxyphenyl)-7-hydroxychromen-4-one.

Sources & evidence

ORD record
ord-fbfba911c8af4d449508660be8352281
Source dataset
uspto-grants-2010_04
Patent number
US07700644B2

Reaction notes

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