Hexane → 4-[(2S)-oxiranylmethoxy]-9-fluorenone

HRID 1634717Notes

Reaction equation

HRID 1634717 reaction equation
CCCCCC.[H-].[K+].[OH:9][C:10]1[C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:23])[C:14]=2[CH:13]=[CH:12][CH:11]=1.S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:28][C@H:29]1[O:31][CH2:30]1)(=O)=O>C1COCC1>[O:31]1[CH2:30][C@H:29]1[CH2:28][O:9][C:10]1[C:22]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:23])[C:14]=2[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 161394-Hydroxy-9-fluorenoneHCID 82127Potassium hydrideHCID 10868995(S)-(+)-Glycidyl-4-nitrobenzoate

Product 1

HCID 590329674-[(2S)-oxiranylmethoxy]-9-fluorenoneYield 16.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred suspension of hexane washed potassium hydride (0.204 g, 5 mmol) in THF was treated in one portion with 4-hydroxy-9-fluorenone (1.0 g, 5.1 mmol). To the purple suspension was added (S)-glycidyl nosylate (1.0 g, 5 mmol) and the mixture was stirred at ambient temperature overnight. The reaction was partitioned with EtOAc. The organic phase was washed with H2O, brine and dried (Na2SO4). The solvent was removed in vacuo to provide crude product. Purification by flash chromatography (CH2Cl2-hexane 3:1) provided 0.210 g of product as a yellow solid.

Workup

  1. customThe reaction was partitioned with EtOAc
  2. washThe organic phase was washed with H2O, brine
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was removed in vacuo
  5. customto provide crude product
  6. customPurification by flash chromatography (CH2Cl2-hexane 3:1)

Sources & evidence

ORD record
ord-15f523dc406745ada8a50e8e7f1d9d47
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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