Hydroxyamine hydrochloride → HCID 73752954, compound

HRID 1384177Notes

Reaction equation

HRID 1384177 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[C:19]([CH3:20])=[CH:18][C:17]3[C:16]([CH3:22])([CH3:21])[CH2:15][CH2:14][C:13]([CH3:24])([CH3:23])[C:12]=3[CH:11]=2)=O)[CH:5]=[CH:6][CH:7]=1.Cl.[NH2:26][OH:27]>N1C=CC=CC=1>[I:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[C:19]([CH3:20])=[CH:18][C:17]3[C:16]([CH3:22])([CH3:21])[CH2:15][CH2:14][C:13]([CH3:24])([CH3:23])[C:12]=3[CH:11]=2)=[N:26][OH:27])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 15428933HCID 15428933, compound

Product 1

HCID 73752954HCID 73752954, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-iodophenyl-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)methanone (6 g, 13.9 mmol), hydroxylamine hydrochloride (4.8 g, 69.5 mmol) and 4 A molecular sieves in pyridine (17 ml) is refluxed for 8 h. The reaction medium is extracted with ethyl acetate and washed with water. After drying, the organic phase is concentrated on a rotary evaporator under vacuum at 40° C. The two isomers (cis and trans) are separated by flash chromatography on a column of silica.

Workup

  1. temperatureis refluxed for 8 h
  2. extractionThe reaction medium is extracted with ethyl acetate
  3. washwashed with water
  4. customAfter drying
  5. concentrationthe organic phase is concentrated on a rotary evaporator under vacuum at 40° C
  6. customThe two isomers (cis and trans) are separated by flash chromatography on a column of silica

Sources & evidence

ORD record
ord-05f775d374d44f5b8315ecdb6a0018b6
Source dataset
uspto-grants-2001_07
Patent number
US06258775B1

Reaction notes

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