Water → Cyclohexanone, 2-[(phenylmethoxy)methyl]-

HRID 1460605Notes

Reaction equation

HRID 1460605 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].Cl[CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH2:16].[CH3:17][CH2:18]OCC>O1CCCC1.[Cl-].[Zn+2].[Cl-]>[C:4]1([CH2:7][O:8][CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C:11]2=[O:16])[CH:18]=[CH:17][CH:1]=[CH:2][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 137983Benzyl chloromethyl etherHCID 178418339Butyllithium

Product 1

HCID 10489011Cyclohexanone, 2-[(phenylmethoxy)methyl]-

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 1-cyclohexenyloxytimethylsilane in dry tetrahydrofuran is treated with n-butyllithium (1.6M in hexane), 1.1 equivalents). After stirring 45 minutes the solution is cooled to 0° C. and a solution of zinc chloride (0.5 equivalents) in tetrahydrofuran is added dropwise. The mixture is stirred for 30 minutes followed by addition of choromethylbenzyl ether (1.2 equivalents) as a solution in tetrahydrofuran. After stirring for 6 hours, water is added. The organics are layered with ether, dried (MgSO4), concentrated in vacuo, then chromatographed to give the title compound.

Workup

  1. stirringThe mixture is stirred for 30 minutes
  2. stirringAfter stirring for 6 hours
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customchromatographed

Sources & evidence

ORD record
ord-cf999f4eb96e49079bd22932521c0dcf
Source dataset
uspto-grants-1991_12
Patent number
US05071853

Reaction notes

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