Isovaleryl chloride → HCID 54517083, compound

HRID 328154Notes

Reaction equation

HRID 328154 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:16]=[CH:15][C:9]([O:10][CH2:11][CH:12]([OH:14])[CH3:13])=[CH:8][CH:7]=1)=[O:5])[CH3:2].[C:17](Cl)(=[O:22])[CH2:18][CH:19]([CH3:21])[CH3:20]>N1C=CC=CC=1>[C:17]([O:14][CH:12]([CH3:13])[CH2:11][O:10][C:9]1[CH:15]=[CH:16][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][CH:8]=1)(=[O:22])[CH2:18][CH:19]([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 66054Isovaleryl chlorideHCID 21444120HCID 21444120, compound

Product 1

HCID 54517083HCID 54517083, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Cooling in an ice bath 1.1g (5 mmol) of 1-(p-ethoxycarbonyl-phenoxy)-propan- 2-ol was dissolved in 10 ml of pyridine, and 0.6 g of isovaleroyl chloride was added dropwise to this solution. The mixture was stirred at room temperature for an additional 3 hours. The reaction mixture was treated in the same way as in Example 7, and purified by column chromatography using silica gel to afford 1.6g of 1-(p-ethoxycarbonyl-phenoxy)-propan-2-ol isovalerate (compound No. 5) in a yield of 90% as a colorless oily substance having an nD32 of 1.4885. Infrared absorption: 1715, 1605, 1260, 1160, 1103, 848 (cm -1).

Workup

  1. additionThe reaction mixture was treated in the same way as in Example 7
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-cd3d6f877c08471380d3c629566b5089
Source dataset
uspto-grants-1977_04
Patent number
US04016186

Reaction notes

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