Diketene → HCID 19894041, compound

HRID 892747Notes

Reaction equation

HRID 892747 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[O:4][N:3]=1.C([O-])(=O)C.[Na+].[CH2:20]=[C:21]1[O:25][C:23](=[O:24])[CH2:22]1>C1C=CC=CC=1>[C:23]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:5]1[O:4][N:3]=[C:2]([CH3:1])[CH:6]=1)(=[O:24])[CH2:22][C:21]([CH3:20])=[O:25]

Participants

5

Reactant 3

HCID 12661DiketeneHCID 517045Sodium AcetateHCID 19894069HCID 19894069, compound

Product 1

HCID 19894041HCID 19894041, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a mixture of 7-(3-methylisoxazol-5-yl)heptan-1-ol (1.97 g, 0.01 mol) and anhydrous sodium acetate (0.080 g) in benzene (20mL) was added a solution of diketene (1.84 g, 0.022 mol) in benzene (6 mL) dropwise. The mixture was refluxed for 12 h. After the removal of benzene under reduced pressure, the crude product was purified by elution from a silica gel column using dichloromethane-hexane (9:1 v/v) as eluant to give 5-(7-acetoacetoxyhept-1-yl)-3-methylisoxazole (21) (70%) as a yellow oil. IR (neat) 1740 (CO2), 1718 (CO)cm-1 ; NMR (CDCl3) 1.12-1.95 (m, 10H, (CH2)5), 2.35 (S, 6H, Me-Het, CO-Me), 2.70 (t, J=9 Hz, 2H, CH2 --Het), 3.49 (S, 2H, CO--CH2 --COMe), 4.14 (t, J=6 Hz, 2H, O--CH2), 5.80 (S, 1H, H-Het). Analysis found: C, 64.11; H, 8.31; N, 4.72. Required: C, 64.02; H, 8.24; N, 5.00 (C15H23NO4). ##STR8##

Workup

  1. temperatureThe mixture was refluxed for 12 h
  2. customAfter the removal of benzene under reduced pressure
  3. customthe crude product was purified by elution from a silica gel column

Sources & evidence

ORD record
ord-9351e32eb89240598494e639c793d982
Source dataset
uspto-grants-1992_06
Patent number
US05120750

Reaction notes

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