Ammonium Hydroxide → HCID 59088101, compound

HRID 989284Notes

Reaction equation

HRID 989284 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][CH:15]([CH:19]=[CH:20][O:21]C)[O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl(O)(=O)(=O)=O.[NH4+].[OH-]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][CH:15]([CH2:19][CH:20]=[O:21])[O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24247Perchloric AcidHCID 69993368HCID 69993368, compound

Product 1

HCID 59088101HCID 59088101, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-(benzyloxy)-2-[2-methoxyethenyl]-chroman (1.0 g, 3.3 mmol) in THF is treated with perchloric acid (0.3 ml), stirred at room temperature for 15 minutes, poured into dilute NH4OH and extracted with ether. The combined extracts are dried over MgSO4 and concentrated in vacuo. The resultant residue is chromatographed (silica gel/20% EtOAc in hexanes as eluent) to give the title product as a colorless oil, 0.484 g (50% yield), identified by NMR and mass spectral analyses.

Workup

  1. extractionextracted with ether
  2. dry with materialThe combined extracts are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue is chromatographed (silica gel/20% EtOAc in hexanes as eluent)

Sources & evidence

ORD record
ord-3198fca2b51f429d9f4990109ee10b97
Source dataset
uspto-grants-2003_10
Patent number
US06638972B2

Reaction notes

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