Dimethoxymethane → HCID 67254607, compound

HRID 2370416Notes

Reaction equation

HRID 2370416 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH2:9][CH2:8][C:7]([CH2:12][OH:13])([CH2:10][OH:11])[C:6]1=[O:14])=[O:4].CO[CH2:25][O:26][CH3:27].[Br-].[Li+].O.[C:31]1(C)C=CC(S(O)(=O)=O)=CC=1.[C:42](=[O:45])([O-])O.[Na+]>C(Cl)(Cl)Cl.C(OCC)C>[CH3:1][O:2][C:3]([C:5]1([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=2)[CH2:9][CH2:8][C:7]([CH2:12][O:13][CH2:27][O:26][CH3:25])([CH2:10][O:11][CH2:31][O:45][CH3:42])[C:6]1=[O:14])=[O:4]

Participants

8

Reactant 5

HCID 8020DimethoxymethaneHCID 82050Lithium BromideHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 67256194HCID 67256194, compound2×

Product 1

HCID 67254607HCID 67254607, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

1-(4-Chlorobenzyl)-3,3-bis-hydroxymethyl-2-oxo-cyclopentancarboxylic acid methyl ester (Compound (XXVI), R2═CH3, Ym=4-Cl) (3.6871 g, 10.0 mmol) was dissolved in chloroform (14.5 ml), combined with dimethoxymethane (14.5 ml), lithium bromide (173.6 mg, 2.00 mmol) and p-toluenesulfonic acid monohydrate (190.2 mg, 1.00 mmol) and stirring was conducted at room temperature for 2 hours. After completion of the reaction, an aqueous solution of sodium hydrogen carbonate and diethyl ether were added, and the organic layer was separated. This was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled away, and the residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=2:1 to 1:1) for purification to obtain the desired substance.

Workup

  1. customAfter completion of the reaction
  2. customthe organic layer was separated
  3. washThis was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled away
  6. customthe residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=2:1 to 1:1) for purification
  7. customto obtain the desired substance

Sources & evidence

ORD record
ord-9e6ce5dd7da546d3a8d64e8cbcd1c671
Source dataset
uspto-grants-2014_04
Patent number
US08710090B2

Reaction notes

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