Sodium hydride → 3,4-Dihydro-7-methoxy-2-naphthaleneacetonitrile

HRID 2286182Notes

Reaction equation

HRID 2286182 reaction equation
[H-].[Na+].C([C:5](CC)(P(O)(O)=O)[C:6]#[N:7])C.[CH3:14][O:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][C:22](=O)[CH2:23]2)=[CH:18][CH:17]=1>C(COC)OC>[CH3:14][O:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][C:22]([CH2:5][C:6]#[N:7])=[CH:23]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 777857-Methoxy-2-tetraloneHCID 21922623Diethyl phosphonoacetonitrile

Product 1

HCID 205418733,4-Dihydro-7-methoxy-2-naphthaleneacetonitrile

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a stirred mixture of 7.1 g. of a 57% mineral oil dispersion of sodium hydride in 400 ml. of dry glyme under nitrogen was added dropwise 28.0 g. of diethyl phosphonoacetonitrile followed by a solution of 25.5 g. of 7-methoxy-2-tetralone in 50 ml. of glyme. After stirring four hours at room temperature the mixture was allowed to stand overnight under nitrogen. The mixture was decanted from an insoluble residue; the supernatant was concentrated in vacuo, and poured into 350 ml. of ice-water. The product was extracted with chloroform and the extracts were washed with water, dried over anhydrous magnesium sulfate and evaporated to dryness to give 29.9 g of 3,4-dihydro-7-methoxy-2-naphthaleneacetonitrile which was converted directly to 7-methoxy-2-naphthaleneacetonitrile as described hereinabove in Example 123.

Workup

  1. additionTo a stirred mixture of 7.1 g
  2. waitto stand overnight under nitrogen
  3. customThe mixture was decanted from an insoluble residue
  4. concentrationthe supernatant was concentrated in vacuo
  5. additionpoured into 350 ml
  6. extractionThe product was extracted with chloroform
  7. washthe extracts were washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-832e45c2dc8449df96424dbd35365e89
Source dataset
uspto-grants-1982_04
Patent number
US04327022

Reaction notes

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