Ammonia → Methyl 6-ethynyl-2-naphthyl-alpha-methylacetate

HRID 840027Notes

Reaction equation

HRID 840027 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15])[CH:7]=[CH:6]2)=[CH2:2].C(Cl)(Cl)Cl.[Br].BrBr.N.[NH2-].[Na+]>C(Cl)(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15])[CH:7]=[CH:6]2)#[CH:2]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 24408BromineHCID 24533Sodium amideHCID 70590429Methyl 6-vinyl-2-naphthyl-alpha-methylacetateHCID 178478473HCID 178478473, compound

Product 1

HCID 86733918Methyl 6-ethynyl-2-naphthyl-alpha-methylacetate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 25.2 g. of methyl 6-vinyl-2-naphthyl-α-methylacetate and 300 ml. of chloroform, a 5% bromine chloroform solution is added at -10° C until the bromine color persists. The mixture is then added to 200 ml. of ammonia containing 15 g. of sodium amide. The mixture is allowed to evaporate; the residue is extracted with diethyl ether. The extracts are combined, washed to neutrality with water, dried, and evaporated to yield methyl 6-ethynyl-2naphthyl-α-methylacetate.

Workup

  1. additionTo a mixture of 25.2 g
  2. additionThe mixture is then added to 200 ml
  3. customto evaporate
  4. extractionthe residue is extracted with diethyl ether
  5. washwashed
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-d7697aa272534c92a0bfc1303d5504f5
Source dataset
uspto-grants-1978_06
Patent number
US04097674

Reaction notes

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