Triethylsilane → (3,4-Dihydroxyphenyl)(morpholino)methanone

HRID 2103116Notes

Reaction equation

HRID 2103116 reaction equation
C1(C2(C3C=CC=CC=3)[O:11][C:10]3[CH:12]=[CH:13][C:14]([C:16]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[O:17])=[CH:15][C:9]=3[O:8]2)C=CC=CC=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[OH:8][C:9]1[CH:15]=[C:14]([C:16]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[O:17])[CH:13]=[CH:12][C:10]=1[OH:11]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 10452791(2,2-Diphenylbenzo[d][1,3]dioxol-5-yl)(morpholino)methanone

Product 1

HCID 21865380(3,4-Dihydroxyphenyl)(morpholino)methanoneYield 95%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of (2,2-diphenyl-benzo[1,3]dioxol-5-yl)-morpholin-4-yl-methanone (270 mg, 0.7 mmol) in trifluoroacetic acid (4 mL) was added triethylsilane (160 mg, 1.38 mmol, 1.96 eq.). The reaction mixture was stirred 20 min at 0° C. The cooling bath was removed and the reaction mixture was stirred for 4 h at R.T. The reaction mixture was evaporated. Purification by flash chromatography afforded the title compound (147 mg, 95%) as a white solid.

Workup

  1. customThe cooling bath was removed
  2. stirringthe reaction mixture was stirred for 4 h at R.T
  3. customThe reaction mixture was evaporated
  4. customPurification by flash chromatography

Sources & evidence

ORD record
ord-06046566397044619b8759febee9891c
Source dataset
uspto-grants-2009_08
Patent number
US07576088B2

Reaction notes

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