4-Fluorophenol → HCID 20164193, compound

HRID 256210Notes

Reaction equation

HRID 256210 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[CH3:15][CH:16]1[N:21](C(OCC2C=CC=CC=2)=O)[CH:20]([CH:32]2[CH2:34][O:33]2)[CH2:19][CH2:18][CH2:17]1>C(O)(C)(C)C.O>[CH3:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH:20]([CH:32]([OH:33])[CH2:34][O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[NH:21]1

Participants

6

Reactant 3

HCID 97324-FluorophenolHCID 20164211HCID 20164211, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20164193HCID 20164193, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of a p-fluorophenol in t-butanol is treated with one equivalent of potassium t-butoxide, followed by the compound of example 35A. The reaction mixture is then refluxed until all epoxide has reacted. The reaction is cooled, diluted with water, and extracted with ethyl acetate. The organic extracts are dried and concentrated. The carbobenzyloxy protecting group is removed by standard hydrogenolysis and the final product purified by chromatography.

Workup

  1. customhas reacted
  2. temperatureThe reaction is cooled
  3. extractionextracted with ethyl acetate
  4. customThe organic extracts are dried
  5. concentrationconcentrated
  6. customThe carbobenzyloxy protecting group is removed by standard hydrogenolysis
  7. customthe final product purified by chromatography

Sources & evidence

ORD record
ord-586bd1bda8364275be67b853aaeca6c6
Source dataset
uspto-grants-1987_10
Patent number
US04701461

Reaction notes

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