Sodium Carbonate → Ethyl 7-oxabicyclo[4.1.0]heptane-3-carboxylate

HRID 1593611Notes

Reaction equation

HRID 1593611 reaction equation
[CH:1]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:20])C=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH:3]12[O:20][CH:4]1[CH2:5][CH2:6][CH:1]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 858033-Cyclohexene-1-carboxylic acid, ethyl ester

Product 1

HCID 15691705Ethyl 7-oxabicyclo[4.1.0]heptane-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl cyclohex-3-ene-1-carboxylate (14.0 g, 90 mmol) in CH2Cl2 (350 mL) was added meta-chloroperbenzoic acid (18.9 g, 110 mmol) at 0° C. The reaction mixture was stirred at room temperature for 2.5 hours. After cooling to 0° C., the reaction was neutralized with aqueous Na2CO3 solution. The organic layer was collected and washed with water and brine, then was dried over MgSO4 and concentrated in vacuo to a light oil (17.8 g), which was used in the next reaction with further purification.

Workup

  1. temperatureAfter cooling to 0° C.
  2. customThe organic layer was collected
  3. washwashed with water and brine
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated in vacuo to a light oil (17.8 g), which
  6. customwas used in the next reaction with further purification

Sources & evidence

ORD record
ord-13244eb723af45c88f98e1c92e42f6fc
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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