Sodium hydride → 3,4-Dihydro-1-methyl-2-naphthaleneacetonitrile
Reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]#[N:13])(=O)OCC)C.[CH3:14][CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17][C:16]1=O>C(COC)OC>[CH3:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][CH2:17][C:16]=1[CH2:11][C:12]#[N:13]Participants
Conditions
- Temperature
- 40 °C
Procedure
To a stirred suspension of 7.2 g (0.15 mole) of sodium hydride (50% in oil dispersion) in 200 ml of dimethoxyethane was added dropwise 28.1 g (0.15 mole) of diethylcyanomethylphosphonate [(C2H5O)2P(O)CH2CN]. The addition was complete in ten minutes while the reaction temperature rose to 44° C. The reaction mixture was stirred for 45 minutes and then 25.0 g (0.14 mole) of 1-methyl-2-tetralone was added dropwise over a 30 minute period. The reaction mixture was then warmed at 40° C. for two hours and poured into ice-water. The product was extracted with ether, and the ether extracts were dried over anhydrous magnesium sulfate and concentrated to a yellow oil (31.3 g). The latter was crystallized from ether-hexane to give 3,4-dihydro-1-methyl-2-naphthaleneacetonitrile as a light yellow solid, m.p. 48°-49° C.
Workup
- additionThe addition
- waitwas complete in ten minutes while the reaction temperature
- customrose to 44° C
- extractionThe product was extracted with ether
- dry with materialthe ether extracts were dried over anhydrous magnesium sulfate
- concentrationconcentrated to a yellow oil (31.3 g)
- customThe latter was crystallized from ether-hexane
Sources & evidence
- ORD record
- ord-a8884dcfb4444c55a494c9916983fd65
- Source dataset
- uspto-grants-1985_09
- Patent number
- US04540705
Reaction notes
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