Water → HCID 22344887, compound

HRID 584034Notes

Reaction equation

HRID 584034 reaction equation
[CH:1]1([CH2:6][C:7]([C:9]2[CH:14]=[C:13]([O:15][C:16]3[C:21]([CH3:22])=[CH:20][C:19]([N+:23]([O-:25])=[O:24])=[CH:18][C:17]=3[CH3:26])[CH:12]=[CH:11][C:10]=2[O:27][CH3:28])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C.O>C(Cl)Cl>[CH:1]1([CH2:6][CH2:7][C:9]2[CH:14]=[C:13]([O:15][C:16]3[C:17]([CH3:26])=[CH:18][C:19]([N+:23]([O-:25])=[O:24])=[CH:20][C:21]=3[CH3:22])[CH:12]=[CH:11][C:10]=2[O:27][CH3:28])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 22344956HCID 22344956, compound

Product 1

HCID 22344887HCID 22344887, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-cyclopentyl-1-[5-(2,6-dimethyl-4-nitro-phenoxy)-2-methoxy-phenyl]-ethanone (200 mg, 0.52 mmol) and trifluoroacetic acid (0.34 mL) in CH2Cl2 (0.5 mL) was added triethylsilane (212 mg, 1.83 mmol). After stirring at RT for 18 h, the reaction mixture was poured into water (15 mL) and extracted with EtOAc (20 mL). The EtOAc extract was washed with sat'd sodium bicarbonate (2×15 mL), brine (15 mL), dried and concentrated. The residue was purified by preparative TLC (CH2Cl2:Hexanes=2:3) to give the title compound of Step B (186 mg) as an oil. MS (APCl−) Calc.: 369.2. Found: 468.3 (M−1).

Workup

  1. extractionextracted with EtOAc (20 mL)
  2. extractionThe EtOAc extract
  3. washwas washed with sat'd sodium bicarbonate (2×15 mL), brine (15 mL)
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC (CH2Cl2:Hexanes=2:3)

Sources & evidence

ORD record
ord-7631a108c2764b43a16a8381ba7680d1
Source dataset
uspto-grants-2005_08
Patent number
US06924310B2

Reaction notes

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