tert-Butanol → HCID 86734622, compound

HRID 328207Notes

Reaction equation

HRID 328207 reaction equation
[N+](C1C=CC(C(OO)=O)=CC=1)([O-])=[O:2].C(O)(C)(C)C.[C:19]([O:22][C:23]1[CH:41]=[CH:40][C:39]2[C@@H:38]3[C@H:28]([C@H:29]4[C@@:33]([CH2:36][CH2:37]3)([CH2:34][CH3:35])[CH:32]=[CH:31][CH2:30]4)[CH2:27][CH2:26][C:25]=2[CH:24]=1)(=[O:21])[CH3:20]>C(Cl)CCl>[C:19]([O:22][C:23]1[CH:41]=[CH:40][C:39]2[C@@H:38]3[C@H:28]([C@H:29]4[C@@:33]([CH2:36][CH2:37]3)([CH2:34][CH3:35])[C@@H:32]3[O:2][C@@H:31]3[CH2:30]4)[CH2:27][CH2:26][C:25]=2[CH:24]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 703424-Nitroperoxybenzoic acidHCID 70634414HCID 70634414, compound

Product 1

HCID 86734622HCID 86734622, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

At room temperature, a solution of 460 mg. of p-nitroperbenzoic acid in 3 ml. of tert.-butanol and 0.6 ml. of ethylene chloride is gradually added to 600 mg. of 3-acetoxy-18-methyl-1,3,5(10),16-estratetraene in 20 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, 490mg. of 3-acetoxy-16α,17α-epoxy-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-685a497a62264f0f933be0b9cdf2e735
Source dataset
uspto-grants-1977_04
Patent number
US04016269

Reaction notes

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