Dimethylformamide → HCID 18922604, compound

HRID 1289877Notes

Reaction equation

HRID 1289877 reaction equation
[Na].[C:2]([C:5]1[O:6][C:7](O)=[CH:8][CH:9]=1)([OH:4])=[O:3].[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Cl)=[CH:15][CH:14]=1.CN([CH:24]=[O:25])C>>[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][O:4][C:2]([C:5]2[O:6][C:7]([CH2:24][OH:25])=[CH:8][CH:9]=2)=[O:3])=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 699934-Methyloxybenzyl chlorideHCID 416153997529-85-6HCID 5360545Sodium

Product 1

HCID 18922604HCID 18922604, compound

Conditions

Temperature
70 °C

Procedure

A mixture of the sodium salt of 2-carboxy-5-hydroxyfuran (3.33 g, 20.28 mmol), 4-methoxybenzyl chloride (3.29 g, 21.0 mmol) and DMF (20 mL) was heated at 70° C. for 5.5 hours. The reaction mixture was poured into ice-water, extracted with ethyl acetate and concentrated to afford 6.3 g of crude product. The crude product was combined with 2.7 g of crude product from a similar experimental run and the mixture was purified by column chromatography on silica gel eluting with 2.5% EtOAc/CH2 Cl2 to 50% EtOAc/CH2Cl2 to afford 5.63 g of 2-(4-methoxyphenylmethyl oxycarbonyl)-5-hydroxymethylfuran.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationconcentrated
  3. customto afford 6.3 g of crude product
  4. customthe mixture was purified by column chromatography on silica gel eluting with 2.5% EtOAc/CH2 Cl2 to 50% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-b3161acd48304bf6a8b7453eb4e25851
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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