Estrone → HCID 9802454, compound

HRID 1576349Notes

Reaction equation

HRID 1576349 reaction equation
[CH3:1][C@@:2]12[C:18](=[O:19])[CH2:17][CH2:16][C@H:15]1[C@H:14]1[C@@H:5]([C:6]3[CH:7]=[CH:8][C:9]([OH:20])=[CH:10][C:11]=3[CH2:12][CH2:13]1)[CH2:4][CH2:3]2.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>N1C=CC=CC=1.O>[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27]([O:20][C:9]2[CH:8]=[CH:7][C:6]3[C@@H:5]4[C@H:14]([C@H:15]5[C@@:2]([CH2:3][CH2:4]4)([CH3:1])[C:18](=[O:19])[CH2:17][CH2:16]5)[CH2:13][CH2:12][C:11]=3[CH:10]=2)(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 5870EstroneHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 9802454HCID 9802454, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Oestrone (2 g., 7.4 mmole) in pyridine (10 ml.) was treated at room temperature for 3 days with toluene-p-sulphonyl chloride (2 g., 1.4 equiv.). The stirred mixture was slowly diluted with water (40 ml.). The precipitated oil slowly crystallized on agitation. Recrystallisation from methanol -- methylene cloride gave the title compound plates (2.65 g., 85%), m.p. 143°-145° , [α]D + 105°. (c, 1.00).

Workup

  1. customThe precipitated oil slowly crystallized on agitation
  2. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-0857355cbf874fab8a6e4b73a24909bf
Source dataset
uspto-grants-1976_09
Patent number
US03980681

Reaction notes

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