Water → HCID 68643656, compound

HRID 1987484Notes

Reaction equation

HRID 1987484 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[SH:16])=O)=[CH:4][CH:3]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O.O>CCCCCC.C(OCC)(=O)C>[SH:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68643648HCID 68643648, compound

Product 1

HCID 68643656HCID 68643656, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a mixture of 0.954 g (4-hydroxyphenyl)(2-mercaptophenyl)methanone (D) (4.0 mmol), 1 ml triethylsilane was added 5 ml TFA. The mixture was stirred at ambient temperature for 1 hour before water was added. The reaction mixture was extracted with ethyl acetate (2×70 ml), brine, dried over magnesium sulfate, filtered and concentrated. Flash silica chromatography (hexane:ethyl acetate 80:20) afforded 0.786 g product (3.5 mmol, 88% yield).

Workup

  1. additionwas added
  2. extractionThe reaction mixture was extracted with ethyl acetate (2×70 ml), brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-adb6aab6c9d04a70acd018312ee025aa
Source dataset
uspto-grants-2009_06
Patent number
US07550505B2

Reaction notes

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