Hydrogen Peroxide → HCID 13075706, compound

HRID 2198539Notes

Reaction equation

HRID 2198539 reaction equation
[OH-].[Na+].OO.C1C[O:8]CC1.[F:10][C:11]([F:44])([F:43])[C:12]([OH:42])([CH2:17][CH2:18][CH2:19][C@H:20]([C@@H:22]1[C@:39]2([CH3:40])[C@H:25]([C@H:26]3[C@H:36]([CH2:37][CH2:38]2)[C@:34]2([CH3:35])[C:29](=[CH:30][C:31](=[O:41])[CH:32]=[CH:33]2)[CH:28]=[CH:27]3)[CH2:24][CH2:23]1)[CH3:21])[C:13]([F:16])([F:15])[F:14]>CO.[Cl-].[Na+].O>[F:10][C:11]([F:43])([F:44])[C:12]([OH:42])([CH2:17][CH2:18][CH2:19][C@H:20]([C@@H:22]1[C@:39]2([CH3:40])[C@H:25]([C@H:26]3[C@H:36]([CH2:37][CH2:38]2)[C@:34]2([CH3:35])[C:29](=[CH:30][C:31](=[O:41])[C@@H:32]4[O:8][C@@H:33]42)[CH:28]=[CH:27]3)[CH2:24][CH2:23]1)[CH3:21])[C:13]([F:15])([F:14])[F:16]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 13075704HCID 13075704, compound

Product 1

HCID 13075706HCID 13075706, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 27 ml of NaOH and 1 ml of 30% H2O2 in degassed MeOH (20 ml) was added a THF solution (10 ml) of 497 mg of the trienone (3) and then the reaction mixture was stirred for 20 hr at room temperature. The reaction mixture was diluted with brine and extracted with ether. The etheral extract was submitted to silica gel column chromatography (AcOEt-n-hexane, 1:4) to give 499 mg (97%) of the epoxide (4): mp 181°-184° C. (from AcOEt-cyclohexane), MS m/e 520(M+), 505, 503; NMR(CDCl3)δ0.70(s, 18-H3), 0.95(d, J=6 Hz, 21-H3), 1.00(s, 19-H3), 3.45 (1H, m, 2-H), 3.62(1H, d, J=6 Hz, 1-H), 4.10(1H, s, OH), 5.62(1H, bs, 4 -H), 6.04(2H, s, 6- and 7-H).

Workup

  1. extractionextracted with ether
  2. extractionThe etheral extract

Sources & evidence

ORD record
ord-8d833acc1d654405b1b44e156d2f1754
Source dataset
uspto-grants-1982_11
Patent number
US04358406

Reaction notes

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