Sodium hydride → 5-Methyl-5,6,7,8,9,10,11,12-Octahydro-5,11-Methano-Benzocyclodecen-13One

HRID 1283909Notes

Reaction equation

HRID 1283909 reaction equation
COC1C=CC2CC3C(=O)C(C)(C=2C=1)CCCC3.[CH3:19][C:20]1([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]Br)[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22][C:21]1=[O:30].[H-].[Na+]>CN(C)C=O>[CH3:19][C:20]12[C:21](=[O:30])[CH:22]([CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=31)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 214100881-Methyl-1-(5-bromopentyl)-2-tetraloneHCID 214101236,7,8,9,10,11-hexahydro-3-methoxy-5-methyl-5,10-methano-5H-benzocyclononen 12-one

Product 1

HCID 214101055-Methyl-5,6,7,8,9,10,11,12-Octahydro-5,11-Methano-Benzocyclodecen-13OneYield 40.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using a procedure analogous to that described in Example X for the preparation of 6,7,8,9,10,11-hexahydro-3-methoxy-5-methyl-5,10-methano-5H-benzocyclononen-12-one there is prepared from 1-methyl-1-(5-bromopentyl)-2-tetralone (19.8 g., 0.0675 mole) and sodium hydride (3.57 g., 0.081 mole, of a 54.5% dispersion in mineral oil) in dimethylformamide (250 ml.); 6.2 g. (40.4%) of the title product, b.p. 126° to 135° C. (0.3 mm.).

Sources & evidence

ORD record
ord-17d5f761ccce4a429c57539ea0573555
Source dataset
uspto-grants-1976_08
Patent number
US03976693

Reaction notes

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