Dimethoxymethane → HCID 67254607, compound

HRID 1752018Notes

Reaction equation

HRID 1752018 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-3dd5e35ae9a34c9d977c8e734995d97e
Source dataset
uspto-grants-2015_10
Patent number
US09162966B2

Reaction notes

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