m-Chloroperbenzoic acid → HCID 70386519, compound

HRID 1639185Notes

Reaction equation

HRID 1639185 reaction equation
C([C:4]1[CH:5]=[CH:6][C:7]2[CH2:8][CH2:9][C@@H:10]3[C@@H:19]([C:20]=2[CH:21]=1)[C@H:18]([O:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:17][C@@:15]1([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]1[O:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])(=O)C.ClC1C=CC=[C:39]([C:43]([O:45]O)=[O:44])C=1.C(=O)(O)[O-].[Na+]>ClCCl>[C:43]([O:45][C:4]1[CH:5]=[CH:6][C:7]2[CH2:8][CH2:9][C@@H:10]3[C@@H:19]([C:20]=2[CH:21]=1)[C@H:18]([O:22][C:23](=[O:28])[C:24]([CH3:26])([CH3:25])[CH3:27])[CH2:17][C@@:15]1([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]1[O:29][C:30](=[O:35])[C:31]([CH3:33])([CH3:32])[CH3:34])(=[O:44])[CH3:39]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 86743523HCID 86743523, compound

Product 1

HCID 70386519HCID 70386519, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the ketone (27) (40 mg. 0.83 mmol) and m-chloroperbenzoic acid (43 mg, 0.248 mmol) in dichloromethane (1 ml) was stirred for four days at room temperature in the dark. Addition of saturated sodium bicarbonate solution was followed by the usual working up procedure with methylene chloride to give a residue which was chromatographed on silica (2 g). Elution with ether-light petroleum (1:20) gave the product (28) (39 mg, 94%), m.p. 143°-146° C. (from ether-light petroleum), νmax 1720 cm-1 (C=O), δ (250 MHz) 7.10 (1 H, d, J 8 Hz, 4-proton), 6.86 (1 H, dd, J 8 and 2.5 Hz, 3-proton), 6.71 (1 H, d, J 2.5 Hz, 1-proton), 5.35 (1 H, dt, J 10.5 and 5 Hz, 11-proton), 4.65 (1 H, dd, J 8.5 and 7.5 Hz, 17-proton), 2.82 (2 H, t, J 7 Hz, 6-proton), 2.54 (1 H, t, J 10.5 Hz, 9-proton), 2.24 (3 H, s, CH3CO), 1.21 (9 H, s, OBut), 1.19 (9 H, s, OBut), 0.89 (3 H, s, 18-CH3), M+ (ammonia chemical ionization) 516 (M+NH3).

Workup

  1. customto give a residue which
  2. customwas chromatographed on silica (2 g)
  3. washElution with ether-light petroleum (1:20)

Sources & evidence

ORD record
ord-e7e030c41f3c4026a31fe8e02f058926
Source dataset
uspto-grants-1989_11
Patent number
US04882439

Reaction notes

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