tert-Butanol → HCID 86734621, compound

HRID 328206Notes

Reaction equation

HRID 328206 reaction equation
[N+](C1C=CC(C(OO)=O)=CC=1)([O-])=O.[C:14]([OH:18])([CH3:17])([CH3:16])C.[OH:19][C:20]1[CH:38]=[CH:37][C:36]2[C@@H:35]3[C@H:25]([C@H:26]4[C@@:30]([CH2:33][CH2:34]3)(CC)[CH:29]=[CH:28]C4)[CH2:24][CH2:23][C:22]=2[CH:21]=1>C(Cl)CCl>[O:18]1[C@H:16]2[C@:30]3([CH2:33][CH2:34][C@H:35]4[C@@H:25]([CH2:24][CH2:23][C:22]5[CH:21]=[C:20]([OH:19])[CH:38]=[CH:37][C:36]=54)[C@@H:26]3[CH2:17][C@@H:14]12)[CH2:29][CH3:28]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 703424-Nitroperoxybenzoic acidHCID 70634020HCID 70634020, compound

Product 1

HCID 86734621HCID 86734621, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

At room temperature, a solution of 360 mg. of p-nitroperbenzoic acid in 2.5 ml. of tert.-butanol and 0.5 ml. of ethylene chloride is gradually added to 450 mg. of 3-hydroxy-18-methyl-1,3,5(10),16-estratetraene in 15 ml. of ethylene chloride. After 18 hours, the crude product is worked up as described in (A) and purified by preparative layer chromatography (eluent: hexane/ethyl acetate = 7 : 3). In this way, 310 mg. of 16α,17α-epoxy-3-hydroxy-18-methyl-1,3,5(10)-estratriene is isolated as an oily product.

Workup

  1. customAt room temperature
  2. custompurified by preparative layer chromatography (eluent: hexane/ethyl acetate = 7 : 3)

Sources & evidence

ORD record
ord-564d72c043284e7189f92a318d2c1923
Source dataset
uspto-grants-1977_04
Patent number
US04016269

Reaction notes

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