Diazoethane → Ethyl 6-methoxymethyloxy-2-naphthyl-alpha-methylacetate

HRID 1576473Notes

Reaction equation

HRID 1576473 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])[CH:9]=[CH:8]2.[N+](=[CH:22][CH3:23])=[N-]>C(OCC)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([CH:15]([CH3:19])[C:16]([O:18][CH2:22][CH3:23])=[O:17])[CH:9]=[CH:8]2

Participants

4

Reactant 2

HCID 70695DiazoethaneHCID 203350726-Methoxymethyloxy-2-naphthyl-alpha-methylacetic acid

Product 1

HCID 70589918Ethyl 6-methoxymethyloxy-2-naphthyl-alpha-methylacetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 26 g. of 6-methoxymethyloxy-2-naphthyl-α-methylacetic acid and 500 ml. of diethyl ether are slowly added a solution comprising of 5.6 g. of diazoethane and 50 ml. of diethyl ether. The reaction mixture is allowed to stand for 15 minutes and then is evaporated under reduced pressure to yield ethyl 6-methoxymethyloxy-2-naphthyl-α-methylacetate. By replacing diazoethane with diazopropane in the above process, propyl 6-methoxymethyloxy-2-naphthyl-α-methylacetate is obtained.

Workup

  1. customis evaporated under reduced pressure

Sources & evidence

ORD record
ord-a0332afe74bb46a5921d2c6863559fb4
Source dataset
uspto-grants-1976_09
Patent number
US03980699

Reaction notes

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