Acetic Anhydride → HCID 131711062, compound

HRID 1679769Notes

Reaction equation

HRID 1679769 reaction equation
[OH:1][C@@:2]1([C:22]#[C:23][CH3:24])[CH:8]=[CH:7][C@H:6]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH2:4][CH3:5])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3.[C:25](OC(=O)C)(=[O:27])[CH3:26]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:25]([O:1][C@@:2]1([C:22]#[C:23][CH3:24])[CH:8]=[CH:7][C@H:6]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH2:4][CH3:5])[C@@H:17]1[C:12](=[CH:13][C:14](=[O:21])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3)(=[O:27])[CH3:26]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 131668063HCID 131668063, compound

Product 1

HCID 131711062HCID 131711062, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Under nitrogen, 250 mg. of 17β-hydroxy-18-methyl-17α-propinyl-4,15-estradien-3-one in 2.5 ml. of pyridine is agitated at room temperature for 2 hours with 1 ml. of acetic anhydride and 10 mg. of 4-(dimethylamino)-pyridine. After the reaction mixture has been worked up as described in Example 36, and after the crude product has been chromatographed on silica gel with acetone-hexane, 110 mg. of 17β-acetoxy-18-methyl-17α-propin-1-yl-4,15-estradien-3-one is obtained.

Workup

  1. customafter the crude product has been chromatographed on silica gel with acetone-hexane, 110 mg

Sources & evidence

ORD record
ord-cabea98594f3460b99a03da2752d60b1
Source dataset
uspto-grants-1978_03
Patent number
US04081537

Reaction notes

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