1,2-Dimethoxyethane → HCID 21427640, compound

HRID 437985Notes

Reaction equation

HRID 437985 reaction equation
[H-].[Na+].C(COC)OC.P(=O)([O-])O[CH2:11][C:12](=[O:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH:17](C)C.[C:23]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]1[C:38]([CH:39]=O)=[C:37]([O:41][CH3:42])[CH:36]=[CH:35][C:34]=1[O:43][CH3:44])([O:25][CH3:26])=[O:24]>C(O)(=O)C>[CH3:44][O:43][C:34]1[CH:35]=[CH:36][C:37]([O:41][CH3:42])=[C:38](/[CH:39]=[CH:11]/[C:12](=[O:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:33]=1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][C:23]([O:25][CH3:26])=[O:24]

Participants

6

Reactant 4

HCID 80711,2-Dimethoxyethane3×HCID 24758Sodium hydrideHCID 21427643HCID 21427643, compoundHCID 178443812HCID 178443812, compound

Product 1

HCID 21427640HCID 21427640, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
85 °C

Procedure

To a slurry of 278 mg. of a dispersion of sodium hydride in mineral oil in 40 ml. of dimethoxyethane is added a solution of 1.33 g. of dimethyl(2-oxoheptyl) phosphonate in 40 ml. of dimethoxyethane and the mixture is stirred for one hour. 1.41 g. of the aldehyde in 40 ml. of dimethoxyethane is added and the mixture heated at 85° C. for eighteen hours. The mixture is then cooled and neutralized with acetic acid and the solvent is removed in vacuo. The residue is then chromatographed on a silica gel column to yield 1,4-dimethoxy-2-(6-carbomethoxyhexyl)-3-(3-oxo-trans-1-octenyl)benzene as a yellow oil.

Workup

  1. temperatureThe mixture is then cooled
  2. customthe solvent is removed in vacuo
  3. customThe residue is then chromatographed on a silica gel column

Sources & evidence

ORD record
ord-48f3f51efa244cb19f259fa96328cf7c
Source dataset
uspto-grants-1977_06
Patent number
US04032656

Reaction notes

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