Pyridine → HCID 53758006, compound

HRID 1679510Notes

Reaction equation

HRID 1679510 reaction equation
O[CH:2]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([CH3:18])[CH3:17])=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].S(Cl)([Cl:29])=O.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>CCOCC>[CH2:6]([O:5][C:3](=[O:4])[CH:2]([Cl:29])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([CH3:18])[CH3:17])=[CH:11][CH:10]=1)[CH3:7]

Participants

6

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 53690882HCID 53690882, compound

Product 1

HCID 53758006HCID 53758006, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In 10 ml of ether, 350 mg of ethyl 2-hydroxy-3-[4-(2-benzoyl-2-propyloxy)phenyl]propionate, 360 mg of thionyl chloride, and catalytic amount of pyridine are added and stirred at room temperature overnight. Then, saturated aqueous sodium bicarbonate solution is added and the ether layer separated is dried, evaporated, and purified with column chromatography. Ethyl-2-chloro-3-[4-(2-benzoyl-2-propyloxy)phenyl]propionate is obtained with the yield of 300 mg. In IR and NMR, this product is in good agreement with the compound No. 1 in Example 7.

Workup

  1. customthe ether layer separated
  2. customis dried
  3. customevaporated
  4. custompurified with column chromatography

Sources & evidence

ORD record
ord-44fb0ecc3013442d8aa27f21a174951b
Source dataset
uspto-grants-1978_03
Patent number
US04080505

Reaction notes

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