Sodium Carbonate → HCID 59032962, compound

HRID 40632

Reaction equation

HRID 40632 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH:5]=[CH:6][CH:7]=[C:8]([OH:11])[C:9]=2[CH:10]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:22](OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O)[C@@H:23]1[O:25][CH2:24]1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.C1COCC1>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8]([O:11][CH2:22][C@@H:23]1[CH2:24][O:25]1)[CH:7]=[CH:6][CH:5]=2

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 146513Benzenesulfonic acid, 3-nitro-, (2R)-2-oxiranylmethyl esterHCID 5902254-Hydroxy-2-methylindoleHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 59032962HCID 59032962, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Methyl-1H-indol-4-ol (0.58 g, 3.9 mmol) and THF (20 mL) were placed in a round bottom flask and stirred at room temperature. Sodium bis(trimethylsilyl) amide (3.9 mL, [1M] in THF) was then slowly added to the reaction mixture. After fifteen minutes of stirring at room temperature (R)-glycidyl-3-nitrobenzenesulfonate was added and the reaction mixture was allowed to stir overnight. Work up of the reaction mixture was carried out with saturated sodium carbonate solution and ethyl acetate. The organic layer was dried with sodium sulfate, filtered and the solvent was removed under reduced pressure to yield a crude oil. The crude oil was purified by flash chromatography (20% Ethyl acetate/heptane) to yield the title compound as a crystalline solid.

Workup

  1. additionwas added
  2. stirringto stir overnight
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customto yield a crude oil
  7. customThe crude oil was purified by flash chromatography (20% Ethyl acetate/heptane)

Sources & evidence

ORD record
ord-ebd93b289be04dc6a4baa50243d59af2
Source dataset
uspto-grants-2013_09
Patent number
US08530475B2

Linked notes

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