Acetonitrile → Dibenzyl ether

HRID 1608439Notes

Reaction equation

HRID 1608439 reaction equation
C([Li])CCC.C(#N)C.[CH2:9]([O:16][C:17]1C=C(OC(CCCC2C=CC=CC=2)C)C=[C:21]2[C:26]=1[CH:25](C(OC1C=CC([N+]([O-])=O)=CC=1)=O)[CH2:24][C:23](C)(C)[CH2:22]2)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[CH2:17]([O:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:26]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 13985546HCID 13985546, compoundHCID 178418339Butyllithium

Product 1

HCID 7657Dibenzyl ether

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 2.4 ml. of 2.1M n-butyllithium in 3.7 ml. tetrahydrofuran at -78° C. is added a solution of 0.26 ml. (5 mmole) acetonitrile in 3.7 ml. THF and the mixture is stirred for one hour. at -78° C. A solution of 1.1 g. (2.0 mmole) p-nitrophenyl 8-benzyloxy-3,3-dimethyl-6 -(5-phenyl-2-pentyloxy)tetralin-1-carboxylate in 3.7 ml. THF is added and stirring continued at -78° C. for 30 minutes. The reaction mixture is warmed to room temperature, quenched with 7 ml. 10% hydrochloric acid and extracted with ethyl ether. Isolation of product as in the preceding Example affords 1.13 g. of crude benzyl ether which gives 500 mg. of purified intermediate by silica gel chromatography: mass spectrum-molecular ion, 495.

Workup

  1. customat -78° C
  2. customquenched with 7 ml
  3. extraction10% hydrochloric acid and extracted with ethyl ether

Sources & evidence

ORD record
ord-d47433440bc84fab8147c79db3fcaca7
Source dataset
uspto-grants-1989_09
Patent number
US04870084

Reaction notes

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