Acetic Acid → 7-(5-chloropentyl)-11-fluoro-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dione

HRID 702887Notes

Reaction equation

HRID 702887 reaction equation
[Br-:14].[Br:10][CH2:11][Br:12].[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][Cl:7].[CH2:36]1[O:37][CH2:38][CH2:39][CH2:40]1.[CH3:41][N:42]1[CH2:43][CH2:44][CH2:45][N:46]([CH3:47])[C:48]1=[O:49].[CH3:52][C:53](=[O:54])[OH:55].[Cu:50][I:51].[F:15][CH:16]1[CH:17]2[CH:18]3[CH2:19][CH2:20][C:21](=[O:35])[CH:22]=[C:23]3[CH:24]=[CH:25][CH:26]2[CH:27]2[CH2:28][CH2:29][C:30](=[O:34])[C:31]2([CH3:32])[CH2:33]1.[I:9].[Li+:13].[Mg:8]>>[CH2:2]([CH2:3][CH2:4][CH2:5][CH2:6][Cl:7])[CH:25]1[CH2:24][C:23]2=[CH:22][C:21](=[O:35])[CH2:20][CH2:19][CH:18]2[CH:17]2[CH:16]([F:15])[CH2:33][C:31]3([CH3:32])[CH:27]([CH:26]21)[CH2:28][CH2:29][C:30]3=[O:34]

Participants

12

Reactant 11

HCID 176Acetic AcidHCID 259Bromide ionHCID 3024DibromomethaneHCID 8028TetrahydrofuranHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24841Hydrogen iodideHCID 28486Lithium ionHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 960701-Bromo-5-chloropentaneHCID 5462224MagnesiumHCID 2195327311-Fluoro-13-methyl-1,2,8,9,10,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,17-dione

Product 1

HCID 1784214457-(5-chloropentyl)-11-fluoro-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dione

Sources & evidence

ORD record
ord-806aa405f9914e22a43c6997e08f1a0f
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (3/10)

Reaction notes

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