Sodium Carbonate → HCID 86751693, compound

HRID 1938774Notes

Reaction equation

HRID 1938774 reaction equation
[C:1]([C@H:6]1[O:10][C@H:9](C(=O)C)[CH2:8][O:7]1)([O:3][CH2:4][CH3:5])=[O:2].ClC1C=CC=[C:17]([C:21]([O:23]O)=[O:22])C=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[C:1]([C@H:6]1[O:10][C@@H:9]([O:23][C:21](=[O:22])[CH3:17])[CH2:8][O:7]1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 67697869HCID 67697869, compound

Product 1

HCID 86751693HCID 86751693, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A 2.5:1 mixture of cis and trans-2-carboethoxy-4-acetyl-1,3-dioxolane (406 mg, 2.16 mmol), 85% meta-chloroperbenzoic acid (mCPBA) (68 mg, 3.81 mmol) and sodium carbonate (389 mg, 3.67 mmol) in dry dichloromethane (10 mL) was stirred under argon for 16 hours at room temperature. The resultant suspension was diluted with dichloromethane and water and stirred for 10 minutes. The aqueous phase was removed and the organic phase was washed successively with saturated sodium thiosulfate, water, brine and then was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the crude product thus obtained was subjected to flash column chromatography (30% EtOAc-Hexanes) to give the title compound (11% yield) which displayed the following spectral characteristics; 1H NMR (CDCl3): δ 1.31 (t, 3H, J=7.2 Hz), 2.07 (s, 1H), 4.15 (d of d, 1H, J=4.5, 9.1 Hz), 4.21-4.29 (m, 3H), 5.42 (s, 1H), 6.39 (d of d, 1H, J=2.4, 4.5 Hz); 13C NMR (CDCl3): δ 14.05, 20.97, 29.69, 71.34, 94.04, 99.80, 167.19, 170.11.

Workup

  1. stirringstirred for 10 minutes
  2. customThe aqueous phase was removed
  3. washthe organic phase was washed successively with saturated sodium thiosulfate, water, brine
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe crude product thus obtained

Sources & evidence

ORD record
ord-d3ba190ec2f44982a59bad0a4260f48f
Source dataset
uspto-grants-1997_12
Patent number
US05693787

Reaction notes

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