Water → HCID 15662546, compound

HRID 2248155Notes

Reaction equation

HRID 2248155 reaction equation
CC(C)=CCO[C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([CH:20]=1)[O:11][CH2:12][CH2:13][NH:14][C:15](=[O:19])[O:16][CH2:17][CH3:18].ClC1C=C[CH:26]=[C:25]([C:29]([O:31]O)=O)[CH:24]=1.[CH3:33]COCC.[OH2:38]>C(Cl)Cl>[CH3:26][C:25]1([CH3:24])[O:31][CH:29]1[CH2:33][O:38][C:7]1[CH:6]=[CH:20][C:10]([O:11][CH2:12][CH2:13][NH:14][C:15](=[O:19])[O:16][CH2:17][CH3:18])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 70297m-Chloroperbenzoic acidHCID 19816571HCID 19816571, compound

Product 1

HCID 15662546HCID 15662546, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To ethyl N-{2[5-(3-methyl-2-butenoxy)phenoxy]ethyl}carbamate (0.46 g, 1.6 mmol) in 10 ml of methylene chloride at 5° is added m-chloroperbenzoic acid (0.29 g, 1.7 mmol) in portions over 15 min. The mixture is stirred at 5° for 1 hour, then allowed to warn to RT and stirred for 1.5 hours longer. Ether is added to the reaction mixture and it is poured into water and washed with 10% sodium sulfite, with saturated sodium bicarbonate, with water until neutral and with brine. The organic layer is dried over calcium sulfate, filtered and rotoevaporated and the residue is purified by Florisil column chromatography to give ethyl N-{2-[4-(3-methyl-2,3-epoxybutoxy)phenoxy]ethyl }carbamate (compound 27, Table A).

Workup

  1. customto warn to RT
  2. stirringstirred for 1.5 hours longer
  3. washwashed with 10% sodium sulfite, with saturated sodium bicarbonate, with water until neutral and with brine
  4. dry with materialThe organic layer is dried over calcium sulfate
  5. filtrationfiltered
  6. customthe residue is purified by Florisil column chromatography

Sources & evidence

ORD record
ord-ce749b99bdac4d8a807e8f06dec37074
Source dataset
uspto-grants-1991_08
Patent number
US05037991

Reaction notes

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