m-Chloroperbenzoic acid → HCID 14677686, compound

HRID 2073554Notes

Reaction equation

HRID 2073554 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:3]=1[CH2:13][CH:14]=[CH:15][CH2:16][OH:17].ClC1C=CC=C(C(OO)=[O:26])C=1>C(Cl)Cl>[OH:26][CH:15]([CH:14]1[O:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:3]=2[CH2:13]1)[CH2:16][OH:17]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 54279647HCID 54279647, compound

Product 1

HCID 14677686HCID 14677686, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of Example 6, (700 mg, 3.0 mmoles) was taken up in about 15 ml CH2Cl2 and cooled to 0° under N2. m-Chloroperbenzoic acid (m-CPBA) was added (660 mg) to the solution and the reaction mixture was stirred 1 hour at 0°. Additional m-CPBA (70 mg) was added and the reaction mixture was stirred for 21 hours at room temperature. Ca(OH)2 (650 mg) was added and the reaction mixture was stirred for 10 minutes then filtered through Celite and concentrated. The residue was taken up in ethyl acetate (10 ml) with Et3N (2 ml) and stirred at room temperature overnight. The concentrate was then concentrated to dryness. Chromatography of the residue on silica gel using ethyl acetate gave the title compound. NMR (90 MHz) (CDCl3) (ppm): 2.5-3.1 (2H, br), 3.20 (2H, d), 3.50 (2H, s), 3.65 (3H, s), 3.6-4.0 (3H, m), 4.70 (1H, m), 6.67 (1H, d), 6.8-7.1 (2H, m).

Workup

  1. temperaturecooled to 0° under N2
  2. stirringthe reaction mixture was stirred for 21 hours at room temperature
  3. stirringthe reaction mixture was stirred for 10 minutes
  4. filtrationthen filtered through Celite
  5. concentrationconcentrated
  6. stirringstirred at room temperature overnight
  7. concentrationThe concentrate was then concentrated to dryness

Sources & evidence

ORD record
ord-afc505908e0f4227afb5bd59edaa70db
Source dataset
uspto-grants-1990_04
Patent number
US04918092

Reaction notes

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