Hydrochloric Acid → HCID 6813148, compound

HRID 1760132Notes

Reaction equation

HRID 1760132 reaction equation
CC([O-])(C)C.[K+].C([O:12][N:13]=O)CC(C)C.[CH2:15]1[CH2:25][C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16]1.Cl>C1COCC1>[C:23]1(=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][C:25]1=[N:13][OH:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 107241-TetraloneHCID 23665647Potassium tert-butoxide

Product 1

HCID 6813148HCID 6813148, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the mixture of t-BuOK (1.2 eq.) in THF at 0° C. was added a solution of isoamylnitrite (1.2 eq.) and α-tetralone (Aldrich) (1.0 eq.) in THF dropwise. The reaction mixture was warmed to RT and stirred at RT for 2 h. The reaction mixture was stripped to dryness, mixed with ice-cooled HCl (1M), extracted with EtOAc, washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified with flash chromatography (silica gel, 2:1 hexane/EtOAc) to give the title compound.

Workup

  1. additionmixed with ice-
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified with flash chromatography (silica gel, 2:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-94bc63bc51674f4d97edec3450c95bbd
Source dataset
uspto-grants-2005_01
Patent number
US06838455B2

Reaction notes

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