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

HRID 1197552Notes

Reaction equation

HRID 1197552 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 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 hours
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customchromatographed

Sources & evidence

ORD record
ord-5b478d646c7e46b28f7fc7cf741cafd9
Source dataset
uspto-grants-1994_01
Patent number
US05276053

Reaction notes

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