Water → HCID 15662546, compound

HRID 1073402Notes

Reaction equation

HRID 1073402 reaction equation
[CH3:1][C:2]([CH3:21])=[CH:3][CH2:4][O:5][C:6]1[CH:20]=[CH:19][C:9]([O:10][CH2:11][CH2:12][NH:13][C:14](=[O:18])[O:15][CH2:16][CH3:17])=[CH:8][CH:7]=1.ClC1C=CC=C(C(OO)=[O:30])C=1.CCOCC.O>C(Cl)Cl>[CH3:21][C:2]1([CH3:1])[O:30][CH:3]1[CH2:4][O:5][C:6]1[CH:20]=[CH:19][C:9]([O:10][CH2:11][CH2:12][NH:13][C:14](=[O:18])[O:15][CH2:16][CH3:17])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 70297m-Chloroperbenzoic acidHCID 14552588HCID 14552588, compound

Product 1

HCID 15662546HCID 15662546, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To ethyl N-{2-[4-(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 warm 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 column chromatography to give ethyl N-{2-[4-(3-methyl-2,3-epoxybutoxy)phenoxy]ethyl}carbamate (compound 27, Table A).

Workup

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

Sources & evidence

ORD record
ord-9984f259f31948348b917bf5c7a80d6d
Source dataset
uspto-grants-1990_11
Patent number
US04968829

Reaction notes

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