Ethyl Acetate → HCID 68895059, compound

HRID 1435772Notes

Reaction equation

HRID 1435772 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([C@H:32]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C@@H:34]([OH:41])[CH2:33]2)=[CH:24]1.C(OCC)(=O)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCCCCCC.C(OCC)(=O)C>[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([C@H:32]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:34](=[O:41])[CH2:33]2)=[CH:24]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 68914861HCID 68914861, compound

Product 1

HCID 68895059HCID 68895059, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21899848Ethylacetate heptaneSolvent

Procedure

Dess-Martin Periodane (1.08 g, 2.55 mmol ) in 10 mL CH2Cl2 was added to (1S,3R)-3-(1H-Indol-3-yl)-indan-1-ol (2.52 mmol ) in 10 mL CH2Cl2 at 0° C. The reaction mixture was allowed to warm to room temperature and stirred 40 min—TLC showed full conversion. To the reaction mixture ethyl acetate and sat. NaHCO3 was added. The organic phase was isolated, washed with 2N NaOH and brine, dried over MgSO4 and concentrated in vacuo. A quantitative yield of (R)-3-(1H-indol-3-yl)-indan-1-one was obtained after flash chromatography (heptane/ethyl acetate, silica gel).

Workup

  1. customThe organic phase was isolated
  2. washwashed with 2N NaOH and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-65d44e2e954b43e4bdc7d59d952822ee
Source dataset
uspto-grants-2009_11
Patent number
US07618967B2

Reaction notes

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