Ethyl Acetate → HCID 58282163, compound

HRID 340862Notes

Reaction equation

HRID 340862 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]([OH:10])([CH3:9])[CH3:8])(=[O:3])[CH3:2].[C:11](Cl)(=[O:15])[C:12](Cl)=[O:13].[C:17]([O:20][CH2:21][CH3:22])(=[O:19])[CH3:18]>N1C=CC=CC=1>[C:1]([O:4][CH2:5][CH2:6][C:7]([O:10][C:11](=[O:15])[C:12]([O:10][C:7]([CH3:8])([CH2:22][CH2:21][O:20][C:17](=[O:19])[CH3:18])[CH3:6])=[O:13])([CH3:9])[CH3:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 65578Oxalyl chlorideHCID 110840221-Acetoxy-3-methyl-3-butanol

Product 1

HCID 58282163HCID 58282163, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of compound (71) (0.322 g, 2.2 mmol) in 10 mL pyridine, oxalyl chloride (0.127 g, 1 mmol) was added slowly and the solution was stirred overnight. 20 mL of ethyl acetate was then added and was washed with 10% ammonium chloride (3×20 mL) followed by brine (1×20 mL). The organic layer was then dried over sodium sulfate, evaporated to dryness and the crude product was collected as an oily, white solid. (0.130 g) 1H NMR (400 MHz, CDCl3): δ 1.57 (s, 12H), 2.04 (s, 6H), 2.19 (t, J=6.8, 4H), 4.20-4.24 (t, J=6.9, 4H).

Workup

  1. washwas washed with 10% ammonium chloride (3×20 mL)
  2. dry with materialThe organic layer was then dried over sodium sulfate
  3. customevaporated to dryness
  4. customthe crude product was collected as an oily, white solid

Sources & evidence

ORD record
ord-ddff79171ecb425e9110c77eed0dd4f5
Source dataset
uspto-grants-2014_11
Patent number
US08895691B2

Reaction notes

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