Sodium hydride → Ammonia
Reaction equation
[H-].[Na+].C1(C)C=CC([S:9]([O:12]CC2CCC(CCC)CC2CCC(CCC)C#[N:27])(=O)=O)=CC=1.[O:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH:33]1[O:38][CH2:39][C:40]1[CH:45]=[CH:44][C:43]([CH2:46][CH2:47][CH3:48])=[CH:42][CH:41]=1.[CH2:49]([CH:52]1[CH2:57][C:56](=[O:58])[O:55][C:53]1=[O:54])[CH2:50][CH3:51].[Al+3].[Cl-:60].[Cl-:61].[Cl-]>>[O:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH:33]1[O:38][CH2:39][C:40]1[CH:41]=[CH:42][C:43]([CH2:46][CH2:47][CH3:48])=[CH:44][C:45]=1[C:56]([CH2:57][CH:52]([CH2:49][CH2:50][CH3:51])[C:53]([OH:55])=[O:54])=[O:58].[O:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH:33]1[O:38][CH2:39][CH:40]1[CH2:41][CH2:42][CH:43]([CH2:46][CH2:47][CH3:48])[CH2:44][CH:45]1[CH2:56][CH2:57][CH:52]([CH2:49][CH2:50][CH3:51])[C:53]([OH:55])=[O:54].[O:12]=[S:9]([Cl:61])[Cl:60].[NH3:27]Participants
Reactant 4
Product 4
Procedure
6 g of NaH (50% in paraffin) are added to a solution of 41.9 g of 2-[2-(2-p-toluenesulfonyloxymethyl-5-propylcyclohexyl)-ethyl]-valeronitrile (obtainable by reaction of p-propylbenzyl 2-tetrahydropyranyl ether with 2-propylsuccinic anhydride/AlCl3 to give 2-(2-tetrahydropyranyloxymethyl-5-propyl-benzoylmethyl)-valeric acid, hydrogenation to 2-[2-(2-tetrahydropyranyloxymethyl-5-propylcyclohexyl)-ethyl]-valeric acid, successive reactions with SOCl2 and NH3 to give 2-[2-(2-hydroxymethyl-5-propylcyclohexyl)-ethyl]-valeric acid amide, dehydration with dicyclohexylcarbodiimide to give the nitrile and tosylation) in 250 ml of dimethylsulfoxide, with stirring; during this addition, the temperature is kept below 35°. The mixture is stirred for a further 2 hours and worked up in the customary manner to give 2-cyano-2,6-dipropyl-trans-decalin.
Sources & evidence
- ORD record
- ord-8c04b765405343d7ae5cb63348a5d129
- Source dataset
- uspto-grants-1986_07
- Patent number
- US04600528
Reaction notes
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