Water → HCID 21468284, compound

HRID 274169Notes

Reaction equation

HRID 274169 reaction equation
[CH3:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)[CH2:3][CH2:4][OH:5].[C:20](Cl)(=[O:24])[CH2:21][CH2:22][CH3:23].O>N1C=CC=CC=1>[CH2:13]([O:12][C:9]1[CH:10]=[CH:11][C:6]([CH:2]([CH3:1])[CH2:3][CH2:4][O:5][C:20](=[O:24])[CH2:21][CH2:22][CH3:23])=[CH:7][CH:8]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8855Butyryl chlorideHCID 14742624HCID 14742624, compound

Product 1

HCID 21468284HCID 21468284, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.56 (10 millimols) of (+)-3-methyl-3-(4benzyloxyphenyl)propanol (XI-1) obtained in Preparation Example (starting material compound (V)) 1, was dissolved in 20 ml of pyridine and 1.38 g (13 millimols) of butyrylchloride was added at 30°-40° C. and reacted for 2 hours. The reaction mixture was poured into 200 ml of water and extracted with 200 ml of toluene and separated and then washed with, in the order, 1N aqueous solution of hydrochloric acid, water, 5% aqueous solution of sodium bicarbonate and water, and thereafter dried on anhydrous magnesium sulfate. After the solvent was distilled out under the reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent: toluene-ethyl acetate) to provide 3.1 g (yield: 95%) of (+)-4-benzyloxy-l-(1-methyl-3-butyryloxypropyl) benzene (VIII-9).

Workup

  1. customreacted for 2 hours
  2. extractionextracted with 200 ml of toluene
  3. customseparated
  4. washwashed with, in the order, 1N aqueous solution of hydrochloric acid, water, 5% aqueous solution of sodium bicarbonate and water
  5. dry with materialdried on anhydrous magnesium sulfate
  6. distillationAfter the solvent was distilled out under the reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (eluent: toluene-ethyl acetate)

Sources & evidence

ORD record
ord-30afa74c9cc14329b72653ea8b067c1d
Source dataset
uspto-grants-1995_02
Patent number
US05389293

Reaction notes

Loading…