Pyridine → HCID 59609081, compound

HRID 1631860Notes

Reaction equation

HRID 1631860 reaction equation
[OH:1][C:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH2:11][OH:12])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].N1C=CC=CC=1.[Cl:25][CH2:26][CH2:27][C:28](Cl)=[O:29].C(OCC)(=O)C>CC(C)=O.O>[C:13]1([C:2]([OH:1])([C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:4])[CH2:11][O:12][C:28](=[O:29])[CH2:27][CH2:26][Cl:25])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 693643-Chloropropionyl chlorideHCID 858062,3-Dihydroxy-1,2-diphenylpropan-1-one

Product 1

HCID 59609081HCID 59609081, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
-10 °C

Procedure

10.2 g (42 mmol) 2,3-dihydroxy-1,2-diphenyl-1-propanone was dissolved in 130 ml acetone. 6.6 g (84 mmol) pyridine was added and the reaction mixture was cooled to −10° C. 10.7 g (84 mmol) 3-chloropropionyl chloride was added drop wise, while the temperature was kept below 0° C. The reaction was allowed to continue for 30 minutes at 0° C., followed by 5 hours at room temperature. 150 ml ethyl acetate and 200 ml water were added to the reaction mixture. The organic fraction was isolated and the aqueous fraction was extracted for a second time with 200 ml ethyl acetate. The pooled organic fractions were dried over MgSO4 and evaporated under reduced pressure. (2,3-diphenyl-2-hydroxy-3-oxopropyl)-3-chloro-propionate was isolated by preparative column chromatography on a Prochorm LC80 column, using Kromasil Si60A 10μ and methylene chloride as eluent at a flow rate of 150 ml/min. 8 g of (2,3-diphenyl-2-hydroxy-3-oxopropyl)-3-chloro-propionate (60%) was isolated as a white crystalline product. (TLC on Merck Kieselgel 254F60, eluent methylene chloride, Rf: 0.19)

Workup

  1. customwas kept below 0° C
  2. waitfollowed by 5 hours at room temperature
  3. customThe organic fraction was isolated
  4. extractionthe aqueous fraction was extracted for a second time with 200 ml ethyl acetate
  5. dry with materialThe pooled organic fractions were dried over MgSO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-340d2d14417f4175a18624f3b016f921
Source dataset
uspto-grants-2014_07
Patent number
US08791289B2

Reaction notes

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